Pyridinyl amides and imides for use as fungicides

ABSTRACT

Compounds of Formula (I), their N-oxides and agriculturally suitable salts are disclosed which are useful as fungicides formula (I), (II) wherein A is a substituted pyridinyl ring; B is a substituted pyridinyl ring; W is C═L or SO n  is O or S; R 1  and R 2  are each independently H; or C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl or C 3 -C 6  cycloalkyl, each optionally substituted; R 3  is H; or C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl or C 3 -C 6  cycloalkyl, C 2 -C 6  alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylaminocarbonyl or C 3 -C 8  dialkylaminocarbonyl; R 4  is C1-C6 alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl or C 3 -C 6  cycloalkyl, each optionally substituted; X is O or S; and n is 1 or 2; provided that when W is C═O and R 1 , R 2  and R 3  are H; then B is other than  4 -trifluoromethyl-3-pyridinyl, 2-chloro-4-pyridinyl and 2,6-dihalo-4-pyridinyl. Also disclosed are compositions containing the compounds of Formula (I) and a method for controlling plant diseases caused by fungal plant pathogens that involves applying an effective amount of a compound of Formula (I).

BACKGROUND OF THE INVENTION

[0001] This invention relates to certain pyridinyl amides and imides,their N-oxides, agriculturally suitable salts and compositions, andmethods of their use as fungicides.

[0002] The control of plant diseases caused by fungal plant pathogens isextremely important in achieving high crop efficiency. Plant diseasedamage to ornamental, vegetable, field, cereal, and fruit crops cancause significant reduction in productivity and thereby result inincreased costs to the consumer. Many products are commerciallyavailable for these purposes, but the need continues for new compounds,which are more effective, less costly, less toxic, environmentally saferor have different modes of action.

[0003] WO 99/42447 discloses certain benzamides of formula i asfungicides

[0004] wherein, among others,

[0005] R¹ is H, alkyl or acyl;

[0006] R² is H or alkyl; and

[0007] L is —(C═O)—, —SO₂— or —(C═S)—.

SUMMARY OF THE INVENTION

[0008] This invention pertains to compounds of Formula I or Formula IIincluding all geometric and stereoisomers, N-oxides, and agriculturallysuitable salts thereof:

[0009] wherein

[0010] A is a substituted pyridinyl ring;

[0011] B is a substituted pyridinyl ring;

[0012] W is C═L or SO_(n);

[0013] L is O or S;

[0014] R¹ and R² are each independently H; or C₁-C₆ alkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl, each optionally substituted;

[0015] R³ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆cycloalkyl, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl;

[0016] R⁴ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆cycloalkyl, each optionally substituted;

[0017] X is O or S; and

[0018] n is 1 or 2; provided that when W is C═O and R¹, R² and R³ are H;then B is other than 4-trifluoromethyl-3-pyridinyl, 2-chloro-4-pyridinyland 2,6-dihalo-4-pyridinyl.

[0019] This invention also relates to fungicidal compositions comprisingfungicidally effective amounts of the compounds of the invention and atleast one additional component selected from the group consisting ofsurfactants, solid diluents or liquid diluents and/or at least one otherfungicide having a different mode of action.

[0020] This invention also relates to a method for controlling plantdiseases caused by fungal plant pathogens comprising applying to theplant or portion thereof, or to the plant seed or seedling, afungicidally effective amount of the compounds of the invention (e.g.,as a composition described herein).

DETAILS OF THE INVENTION

[0021] As noted above, A and B are each independently a substitutedpyridinyl ring. The term “substituted” in connection with these A or Bgroups refers to groups that have at least one non-hydrogen substituentthat does not extinguish the fungicidal activity. Examples of Formula Iand Formula II incorporating said pyridinyl rings in which A issubstituted with 1 to 4 R⁵, B is substituted with 1 to 4 R⁶ include therings illustrated in Exhibit 1 wherein m and p are independentlyintegers from 1 to 4. Note that the attachment point between (R⁵)_(m)and A and (R⁶)_(p) and B is illustrated as floating, and (R⁵)_(m) and(R⁶)_(p) can be attached to any available carbon atom of the pyridinylrings.

[0022] Examples of R⁵ when attached to A and R⁶ when attached to Binclude:

[0023] R⁵ and R⁶ are each independently C₁-C₆ alkyl, C₂-C₆ alkenyl,C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,C₂-C₆ haloalkyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂,hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkoxycarbonyl, C₁-C₄alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈dialkylaminocarbonyl, C₃-C₆ trialkylsilyl; or

[0024] R⁵ and R⁶ are each independently phenyl, benzyl or phenoxy, eachoptionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl,C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl,C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy,C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl C₁-C₄alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl,C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈dialkylaminocarbonyl or C₃-C₆ trialkylsilyl.

[0025] Other R⁵ and R⁶ groups will be evident to one of ordinary skill.For example, each R⁵ and/or R⁶ can be NH₂, NHCO(C₁-C₄ alkyl) orNHCO(C₁-C₄ haloalkyl); or each R⁵ and/or R⁶ can be phenyl, benzyl orphenoxy, each substituted with C₅-C₈ trialklylsilylalkynyl.

[0026] Of note are compounds of Formula I wherein

[0027] R⁵ and R⁶ are each independently C₁-C₆ alkyl, C₂-C₆ alkenyl,C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂,hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkoxycarbonyl, C₁-C₄alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈dialkylaminocarbonyl, C₃-C₆ trialkylsilyl; or

[0028] R⁵ and R⁶ are each independently phenyl, benzyl or phenoxy, eachoptionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl,C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl,C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy,C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl C₁-C₄alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl,C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈dialkylaminocarbonyl, C₅-C₈ trialklylsilylalkynyl or C₃-C₆trialkylsilyl.

[0029] As noted above, R¹ and R² are each independently H; or C₁-C₆alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl, each optionallysubstituted; and R4 is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl orC₃-C₆ cycloalkyl, each optionally substituted. The term “optionallysubstituted” in connection with these R¹, R² and R⁴ groups refers togroups which are unsubstituted or have at least one non-hydrogensubstituent that does not extinguish the fungicidal activity possessedby the unsubstituted analog. Examples of optionally substituted R¹, R²and R⁴ groups are those that are optionally substituted with one or moresubstituents selected from the group consisting of halogen, CN, NO₂,hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄alkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈dialkylamino and C₃-C₆ cycloalkylamino. Although these substituents arelisted in the examples above, it is noted that they do not need to bepresent since they are optional substituents.

[0030] Examples of N-oxides of Formula I or Formula II are illustratedas I-10 through I-16 and as II-10 through II-16, respectively, inExhibit 2, wherein R¹, R², R³, R⁴, R⁵, R⁶, W, X, m and p are as definedabove.

[0031] In the above recitations, the term “alkyl”, used either alone orin compound words such as “alkylthio” or “haloalkyl” includesstraight-chain or branched alkyl, such as, methyl, ethyl, n-propyl,i-propyl, or the different butyl, pentyl or hexyl isomers. The term “1-2alkyl” indicates that one or two of the available positions for thatsubstituent may be alkyl which are independently selected. “Alkenyl”includes straight chain or branched alkenes such as ethenyl, 1-propenyl,2-propenyl, and the different butenyl, pentenyl and hexenyl isomers.“Alkenyl” also includes polyenes such as 1,2-propadienyl and2,4-hexadienyl. “Alkynyl” includes straight chain or branched alkynessuch as ethynyl, 1-propynyl, 2-propynyl and the different butynyl,pentynyl and hexynyl isomers. “Alkynyl” can also include moietiescomprised of multiple triple bonds such as 2,5-hexadiynyl. “Alkoxy”includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy andthe different butoxy, pentoxy and hexyloxy isomers. “Alkoxyalkyl”denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” includeCH₃OCH₂, CH₃OCH₂CH₂, CH₃CH₂OCH₂, CH₃CH₂CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂.“Alkoxyalkoxy” denotes alkoxy substitution on alkoxy. The term“Alkenyloxy” includes straight chain or branched alkenyloxy moieties.Examples of “alkenyloxy” include H₂C═CHCH₂O, (CH₃)₂C═CHCH₂O,(CH₃)CH═CHCH₂O, (CH₃)CH═C(CH₃)CH₂O and CH₂═CHCH₂CH₂O. “Alkynyloxy”includes straight chain or branched alkynyloxy moieties. Examples of“alkynyloxy” include HC≡CCH₂O, CH₃C—CCH₂O and CH₃C═CCH₂CH₂O. “Alkylthio”includes branched or straight chain alkylthio moieties such asmethylthio, ethylthio, and the different propylthio, butylthio,pentylthio and hexylthio isomers. “Alkylthioalkyl” denotes alkylthiosubstitution on alkyl. Examples of “alkylthioalkyl” include CH₃SCH₂,CH₃SCH₂CH₂, CH₃CH₂SCH₂, CH₃CH₂CH₂CH₂SCH₂ and CH₃CH₂SCH₂CH₂.“Alkylthioalkoxy” denotes alkylthio substitution on alkoxy.“Alkylsulfinyl” includes both enantiomers of an alkylsulfinyl group.Examples of “alkylsulfinyl” include CH₃S(O), CH₃CH₂S(O), CH₃CH₂CH₂S(O),(CH₃)₂CHS(O) and the different butylsulfinyl, pentylsulfinyl andhexylsulfinyl isomers. Examples of “alkylsulfonyl” include CH₃S(O)₂,CH₃CH₂S(O)₂, CH₃CH₂CH₂S(O)₂, (CH₃)₂CHS(O)₂ and the differentbutylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. “Cyanoalkyl”denotes an alkyl group substituted with one cyano group. Examples of“cyanoalkyl” include NCCH₂, NCCH₂CH₂ and CH₃CH(CN)CH₂. “Alkylamino”,“dialkylamino”, “alkenylthio”, “alkenylsulfinyl”, “alkenylsulfonyl”,“alkynylthio”, “alkynylsulfinyl”, “alkynylsulfonyl”, and the like, aredefined analogously to the above examples. “Cycloalkyl” includes, forexample, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The term“cycloalkoxy” includes the same groups linked through an oxygen atomsuch as cyclopentyloxy and cyclohexyloxy.

[0032] The term “halogen”, either alone or in compound words such as“haloalkyl”, includes fluorine, chlorine, bromine or iodine. The term“1-2 halogen” indicates that one or two of the available positions forthat substituent may be halogen which are independently selected.Further, when used in compound words such as “haloalkyl”, said alkyl maybe partially or fully substituted with halogen atoms which may be thesame or different. Examples of “haloalkyl” include F₃C, ClCH₂, CF₃CH₂and CF₃CCl₂. The terms “haloalkenyl”, “haloalkynyl”, “haloalkoxy”,“haloalkylthio”, and the like, are defined analogously to the term“haloalkyl”. Examples of “haloalkenyl” include (Cl)₂C═CHCH₂ andCF₃CH₂CH═CHCH₂. Examples of “haloalkynyl” include HC≡CCHCl, CF₃C≡C,CCl₃C≡C and FCH₂C≡CCH₂. Examples of “haloalkoxy” include CF₃O, CCl₃CH₂O,HCF₂CH₂CH₂O and CF₃CH₂O. Examples of “haloalkylthio” include CCl₃S,CF₃S, CCl₃CH₂S and ClCH₂CH₂CH₂S. Examples of “haloalkylsulfinyl” includeCF₃S(O), CCl₃S(O), CF₃CH₂S(O) and CF₃CF₂S(O). Examples of“haloalkylsulfonyl” include CF₃S(O)₂, CCl₃S(O)₂, CF₃CH₂S(O)₂ andCF₃CF₂S(O)₂. Examples of “haloalkoxyalkoxy” include CF₃OCH₂O,ClCH₂CH₂OCH₂CH₂O, Cl₃CCH₂OCH₂O as well as branched alkyl derivatives.Examples of “alkylcarbonyl” include C(O)CH₃, C(O)CH₂CH₂CH₃ andC(O)CH(CH₃)₂. Examples of “alkoxycarbonyl” include CH₃C(—O),CH₃CH₂C(═O), CH₃CH₂CH₂C(═O), (CH₃)₂CHOC(═O) and the different butoxy- orpentoxycarbonyl isomers.

[0033] One skilled in the art will appreciate that not all nitrogencontaining heterocycles can form N-oxides since the nitrogen requires anavailable lone pair for oxidation to the oxide; one skilled in the artwill recognize those nitrogen containing heterocycles which can formN-oxides. One skilled in the art will also recognize that tertiaryamines can form N-oxides. Synthetic methods for the preparation ofN-oxides of heterocycles and tertiary amines are very well known by oneskilled in the art including the oxidation of heterocycles and tertiaryamines with peroxy acids such as peracetic and m-chloroperbenzoic acid(MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butylhydroperoxide, sodium perborate, and dioxiranes such asdimethydioxirane. These methods for the preparation of N-oxides havebeen extensively described and reviewed in the literature, see forexample: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik inComprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boultonand A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keenein Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. RKatritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advancesin Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J.Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G.Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A.R Katritzky and A. J. Boulton, Eds., Academic Press.

[0034] The total number of carbon atoms in a substituent group isindicated by the “C_(i)-C_(j)” prefix where i and j are numbers from 1to 8. For example, C₁-C₃ alkylsulfonyl designates methylsulfonyl throughpropylsulfonyl; C₂ alkoxyalkyl designates CH₃OCH₂; C₃ alkoxyalkyldesignates, for example, CH₃CH(OCH₃), CH₃OCH₂CH₂ or CH₃CH₂OCH₂; and C₄alkoxyalkyl designates the various isomers of an alkyl group substitutedwith an alkoxy group containing a total of four carbon atoms, examplesincluding CH₃CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂.

[0035] When a compound is substituted with a substituent bearing asubscript that indicates the number of said substituents can exceed 1,said substituents (when they exceed 1) are independently selected fromthe group of defined substituents. Further, when the subscript indicatesa range, e.g. (R)_(i-j), then the number of substituents may be selectedfrom the integers between i and j inclusive.

[0036] When a group contains a substituent which can be hydrogen, forexample R¹ or R² then, when this substituent is taken as hydrogen, it isrecognized that this is equivalent to said group being unsubstituted.

[0037] Compounds of this invention can exist as one or morestereoisomers. The various stereoisomers include enantiomers,diastereomers, atropisomers and geometric isomers. One skilled in theart will appreciate that one stereoisomer may be more active and/or mayexhibit beneficial effects when enriched relative to the otherstereoisomer(s) or when separated from the other stereoisomer(s).Additionally, the skilled artisan knows how to separate, enrich, and/orto selectively prepare said stereoisomers. Accordingly, the presentinvention comprises compounds selected from Formula I, N-oxides andagriculturally suitable salts thereof. The compounds of the inventionmay be present as a mixture of stereoisomers, individual stereoisomers,or as an optically active form. In particular, when R¹ and R² of FormulaI and Formula II are different, then said formulas possess a chiralcenter at the carbon to which they are commonly bonded. This inventioncomprises racemic mixtures. In addition, this invention includescompounds that are enriched compared to the racemic mixture in anenantiomer of the formulas

[0038] Included are the essentially pure enantiomers of Formula I′ andFormula II′. This invention also includes compounds that are enrichedcompared to the racemic mixture in an enantiomer of the formulas

[0039] Included are the essentially pure enantiomers of Formula I″ andFormula II″.

[0040] When enantiomerically enriched, one enantiomer is present ingreater amounts that the other and the extent of enrichment can bedefined by an expression of enantiomer excess(“ee”), which is defined as100 (2x−1) where x is the mole fraction of the dominant enantiomer inthe mixture. (e.g., an ee of 20% corresponds to a 60:40 ratio ofenantiomers).

[0041] The more active enantiomer with respect to the relative positionsof R¹, R², A and the rest of the molecule bonded through nitrogencorresponds to the configuration of the enantiomer of2,4-dichloro-N-[(1R)-1-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl]-3-pyridinecarboxamidethat, when in a solution of CDCl₃, rotates plane polarized light in the(+) or detxio direction (i.e. the predominant enantiomer of Compound 31of Index Table B).

[0042] Preferably the compositions of this invention have at least a 50%enantiomeric excess; more preferably at least a 75% enantiomeric excess;still more preferably at least a 90% enantiomeric excess; and the mostpreferably at least a 94% enantiomeric excess of the more active isomer.Of particular note are enantiomerically pure embodiments of the moreactive isomer.

[0043] Compounds of Formula II can also exist as (E)- or (Z)-isomers, oras a mixture of E)- and (Z)-isomers with respect to the C═N bond shownin the structure. This invention comprises mixtures of geometric isomersas well as the individual isomers.

[0044] The salts of the compounds of the invention include acid-additionsalts with inorganic or organic acids such as hydrobromic, hydrochloric,nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic,malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic orvaleric acids. The salts of the compounds of the invention also includethose formed with organic bases (e.g., pyridine, ammonia, ortriethylamine) or inorganic bases (e.g., hydrides, hydroxides, orcarbonates of sodium, potassium, lithium, calcium, magnesium or barium)when the compound contains an acidic group such as a carboxylic acid orphenol.

[0045] Preferred compounds for reasons of better activity and/or ease ofsynthesis are:

[0046] Preferred 1. Preferred are compounds of Formula I or Formula IIwherein

[0047] A is a pyridinyl ring substituted with from 1 to 4 R⁵;

[0048] B is a pyridinyl ring substituted with from 1 to 4 R⁶;

[0049] R¹ and R² are each independently H; or C₁-C₆ alkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl, each optionally substitutedwith one or more substituents selected from the group consisting ofhalogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₁-C₄alkylamino, C₂-C₈ dialkylamino and C₃-C₆ cycloalkylamino;

[0050] R⁴ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆cycloalkyl, each optionally substituted with one or more substituentsselected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C₄alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino and C₃-C₆cycloalkylamino; and

[0051] R⁵ and R⁶ are each independently C₁-C₆ alkyl, C₂-C₆ alkenyl,C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂,hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkoxycarbonyl, C₁-C₄alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈dialkylaminocarbonyl, C₃-C₆ trialkylsilyl; or

[0052] R⁵ and R⁶ are each independently phenyl, benzyl or phenoxy, eachoptionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl,C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl,C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy,C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl C₁-C₄alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl,C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈dialkylaminocarbonyl or C₃-C₆ trialkylsilyl.

[0053] Of note are compounds of Preferred 1 wherein

[0054] each R⁵ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂,hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkoxycarbonyl, C₁-C₄alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈dialkylaminocarbonyl, C₃-C₆ trialkylsilyl; provided that when A is2-pyridinyl, then R⁵ is other than C₁ to C₆ haloalkyl; and

[0055] each R⁶ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆haloalkynyl C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂,hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄haloalkylsulfinyl C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkoxycarbonyl, C₁-C₄alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈dialkylaminocarbonyl, C₃-C₆ trialkylsilyl; or

[0056] R⁵ and R⁶ are each independently phenyl, benzyl or phenoxy, eachoptionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl,C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl,C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy,C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl C₁-C₄alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl,C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈dialkylaminocarbonyl or C₃-C₆ trialkylsilyl.

[0057] Preferred 2. Compounds of Preferred 1 of Formula I wherein W isC═O.

[0058] Of note are compounds of Preferred 2 wherein A is a substituted3-pyridinyl ring. Also of note are compounds of Preferred 2 wherein

[0059] each R⁵ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂,hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl C₁-C₄ haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkoxycarbonyl, C₁-C₄alkylamino, C₂-Cg dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈dialkylaminocarbonyl, C₃-C₆ trialkylsilyl; provided that when A is2-pyridinyl, then R⁵ is other than C₁ to C₆ haloalkyl.

[0060] Preferred 3. Compounds of Preferred 2 wherein

[0061] A is a 2-pyridinyl ring substituted with from 1 to 4 R⁵; and

[0062] B is substituted with from 1 to 4 R⁶, with at least one R⁶located in a position ortho to the link with W.

[0063] Of note are compounds of Preferred 3 wherein R⁵ is Cl, Br, CH₃,OCF₃, OCHF₂, OCH₂CF₃, OCF₂CF₃, OCF₂CF₂H, OCHFCF₃, SCF₃, SCHF₂, SCH₂CF₃,SCF₂CF₃, SCF₂CF₂H, SCHFCF₃, SOCF₃, SOCHF₂, SOCH₂CF₃, SOCF₂CF₃,SOCF₂CF₂H, SOCHFCF₃, SO₂CF₃, SO₂CHF₂, SO₂CH₂CF₃, SO₂CF₂CF₃, SO₂CF₂CF₂Hor SO₂CHFCF₃. Also of note are compounds of Preferred 3 wherein B iseither a 3-pyridinyl or 4-pyridinyl ring having an R⁶ at each positionortho to the link with W (and optionally 1 to 2 additional R⁶).

[0064] Preferred 4. Compounds of Preferred 3 wherein B is either a3-pyridinyl or 4-pyridinyl ring having an R⁶ at each position ortho tothe link with W, and optionally 1 to 2 additional R⁶ and R⁶ is eitherhalogen or methyl.

[0065] Preferred 5. Compounds of Preferred 4 wherein B is a 3-pyridinylring wherein one R⁶ is Cl and is located at the 2-position ortho to thelink with W, another R⁶ is selected from Cl or methyl and is located atthe 4-position ortho to the link with W and a third optional R⁶ ismethyl at the 6-position.

[0066] Preferred 6. Compounds of Preferred 5 wherein A is3-chloro-5-CF₃-2-pyridinyl.

[0067] Preferred 7. Compounds of Preferred 3, but especially Preferred4, wherein R¹ is H and R² is CH₃.

[0068] Preferred 8. Compounds of Preferred 1 of Formula II wherein

[0069] A is a 2-pyridinyl ring substituted with from 1 to 4 R⁵; and

[0070] B is substituted with from 1 to 4 R⁶, with at least one R⁶located in a position ortho to the link with the carbon that is bondedto both X and B.

[0071] Preferred 9. Compounds of Preferred 5 wherein X is S.

[0072] Preferred compounds of this invention include those of Preferred1 through Preferred 9 wherein R¹ is H or CH₃, R² is H and (in Formula I)R³ is H.

[0073] Specifically preferred are the compounds selected from the groupconsisting of

[0074]2,4-Dichloro-N-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl]-3-pyridinecarboxamide,

[0075]2,4-Dichloro-N-[1-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl]-3-pyridinecarboxamide,

[0076]2,4-Dichloro-N-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl]-6-methyl-3-pyridinecarboxamide,and

[0077]2,4-Dichloro-N-[1-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl]-6-methyl-3-pyridinecarboxamide.

[0078] Also specifically preferred are the compounds selected from thegroup consisting of

[0079]2,4-Dichloro-N-[(3,5-dichloro-2-pyridinyl)methyl]-3-pyridinecarboxamide,

[0080]2,4-Dichloro-N-[1-(3,5-dichloro-2-pyridinyl)ethyl]-3-pyridinecarboxamide,

[0081]2,4-Dichloro-N-[(3,5-dichloro-2-pyridinyl)methyl]-6-methyl-3-pyridinecarboxamide,

[0082]2,4-Dichloro-N-[1-(3,5-dichloro-2-pyridinyl)ethyl]-6-methyl-3-pyridinecarboxamide,

[0083]N-[(5-bromo-3-chloro-2-pyridinyl)methyl]-2,4-dichloro-3-pyridinecarboxamide,

[0084]N-[1-(5-bromo-3-chloro-2-pyridinyl)ethyl]-2,4-dichloro-3-pyridinecarboxamide,

[0085]N-[(5-bromo-3-chloro-2-pyridinyl)methyl]-2,4-dichloro-6-methyl-3-pyridinecarboxamide,and

[0086]N-[1-(5-bromo-3-chloro-2-pyridinyl)ethyl]-2,4-dichloro-6-methyl-3-pyridinecarboxamide.

[0087] This invention also relates to fungicidal compositions comprisingfungicidally effective amounts of the compounds of the invention and atleast one additional component selected from the group consisting ofsurfactants, solid diluents or liquid diluents. The preferredcompositions of the present invention are those which comprise the abovepreferred compounds.

[0088] This invention also relates to a method for controlling plantdiseases caused by fungal plant pathogens comprising applying to theplant or portion thereof, or to the plant seed or seedling, afungicidally effective amount of the compounds of the invention (e.g.,as a composition described herein). The preferred methods of use arethose involving the above-preferred compounds.

[0089] The compounds of Formula I and Formula II can be prepared by oneor more of the following methods and variations as described in Schemes1-6. The definitions of A, B, L, W, R¹ through R⁶, X and n in thecompounds of Formulas 1-4 below are as defined above. Compounds ofFormula 1a, 1b and 1c are subsets of Formula 1. Compounds of FormulaeIa, Ib and Ic are subsets of the compounds of Formula I, and allsubstituents for Formulae Ia, Ib and Ic are as defined above for FormulaI. Compounds of Formula IIa are a subset of the compounds of Formula II,and all substituents for Formula IIa are as defined above for FormulaII.

[0090] The compounds of Formula I can be prepared as described below inSchemes 1-5. The compounds of Formula Ic and IIa can be prepared asdescribed below in Scheme 6.

[0091] The compounds of Formula Ia are prepared by treating amine saltsof Formula 1 with an appropriate acid chloride in an inert solvent withtwo molar equivalents of a base (e.g. triethylamine or potassiumcarbonate) present. Suitable solvents are selected from the groupconsisting of ethers such as tetrahydrofuran, dimethoxyethane, ordiethyl ether; hydrocarbons such as toluene or benzene; and halocarbonssuch as dichloromethane or chloroform.

[0092] Alternatively, compounds of Formula Ia can be synthesized byreacting the amine salts of Formula 1 with an appropriate carboxylicacid in the presence of an organic dehydrating reagent such as1,3-dicyclohexylcarbodiimide (DCC) or1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) asdepicted in Scheme 2. Suitable solvents are selected from the groupconsisting of ethers such as tetrahydrofuran, dimethoxyethane, ordiethyl ether; hydrocarbons such as toluene or benzene; and halocarbonssuch as dichloromethane or chloroform.

[0093] Intermediate salt 1a, wherein A is 2-pyridyl bearing theindicated substituents and R¹, R², and R³ are hydrogen, can be preparedby reacting the commercially available imine ester 5 shown in Scheme 3with a 2,3-dichloro-pyridine substituted with R⁵ (of Formula 4) in thepresence of a strong base such as sodium hydride in a polar, aproticsolvent such as N,N-dimethylformamide followed by heating in acidicmedium in a procedure analogous to those found in WO99/42447. Compoundsof Formula 1b can be prepared by similar procedures in which theintermediate anion resulting from step 1 is treated with an alkylatingagent such as methyl iodide prior to heating in an acidic medium. Ofnote are compounds wherein R⁵ is CF₃.

[0094] Compounds of Formula 1c (wherein A is a substituted pyridinylring), bearing an aminomethyl group, can be synthesized from nitrites ofFormula 2 (wherein A is a substituted pyridinyl ring) by reduction ofthe nitrile using lithium aluminum hydride in toluene to give thecorresponding aminomethyl intermediates (Scheme 4).

[0095] A is a substituted pyridinyl ring

[0096] Alternatively, compounds of Formula 1c (compounds in which A isas defined above and R¹ and R² are hydrogen) can be synthesized byreacting compounds of Formula 3 with ammonia in a protic solvent such asmethanol to provide compounds of Formula 1c. Compounds of Formula 1c canalso be prepared by reacting compounds of Formula 3 with a potassiumsalt of phthalimide followed by reaction with either aminoethanol orhydrazine in an alcohol solvent to provide the desired aminomethylintermediates, Formula 1c (Scheme 5).

[0097] Compounds of Formula IIa (compounds in which R¹, R², A and B areas defined above and X is S) can be synthesized as outlined in Scheme 6.Amides of Formula Ib (compounds of Formula I in which R³ is H) shownbelow can be converted to thioamides of Formula Ic by contacting theamide with Lawesson's reagent or phosphorus pentasulfide in anappropriate solvent (for references, see March; J. Advanced OrganicChemistry, 4^(th) ed., pp. 893-4). The thioamide can then be alkylatedusing an appropriate alkylating reagent in the presence of a base suchas potassium carbonate, sodium hydride or potassium hydroxide. Suitablesolvents can include, but are not limited to, ethers such astetrahydrofuran, dimethoxyethane, or diethyl ether; hydrocarbons such astoluene or benzene; and halocarbons such as dichloromethane orchloroform.

[0098] It is recognized that some reagents and reaction conditionsdescribed above for preparing compounds of Formula I may not becompatible with certain functionalities present in the intermediates. Inthese instances, the incorporation of protection/deprotection sequencesor functional group interconversions into the synthesis will aid inobtaining the desired products. The use and choice of the protectinggroups will be apparent to one skilled in chemical synthesis (see, forexample, Greene, T. W.; Wuts, P. G. M. Protective Groups in OrganicSynthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art willrecognize that, in some cases, after the introduction of a given reagentas it is depicted in any individual scheme, it may be necessary toperform additional routine synthetic steps not described in detail tocomplete the synthesis of compounds of Formula I. One skilled in the artwill also recognize that it may be necessary to perform a combination ofthe steps illustrated in the above schemes in an order other than thatimplied by the particular sequence presented to prepare the compounds ofFormula I.

[0099] One skilled in the art will also recognize that compounds ofFormula I and the intermediates described herein can be subjected tovarious electrophilic, nucleophilic, radical, organometallic, oxidation,and reduction reactions to add substituents or modify existingsubstituents.

[0100] Without further elaboration, it is believed that one skilled inthe art using the preceding description can utilize the presentinvention to its fullest extent. The following Examples are, therefore,to be construed as merely illustrative, and not limiting of thedisclosure in any way whatsoever. Percentages are by weight except forchromatographic solvent mixtures or where otherwise indicated. Parts andpercentages for chromatographic solvent mixtures are by volume unlessotherwise indicated. ¹H NMR spectra are reported in ppm downfield fromtetramethylsilane; s is singlet, d is doublet, t is triplet, q isquartet, m is multiplet, dd is doublet of doublets, dt is doublet oftriplets, br s is broad singlet.

EXAMPLE 1 Preparation of2,4-Dichloro-N-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl]-6-methyl-3-pyridinecarboxamide(Compound8 of Index Table B):

[0101] Step A: Preparation of2,4-Dichloro-N-[[3-chloro-5-(trifluoromethyl-2-pyridinyl]methyl]-6-methyl-3-pyridinecarboxamide

[0102] Compound 8 was prepared by using2-aminomethyl-3-chloro-5-trifluoromethylpyridine hydrochloride (preparedas described in WO99/42447). 2,4-dichloro-6-methyl-3-pyridine carbonylchloride (0.65 g) in 2 mL of methylene chloride was added to a solutionof 2-aminomethyl-3-chloro-5-trifluoromethylpyridine hydrochloride (0.79g) and triethylamine (0.68 g) in 10 mL of methylene chloride at roomtemperature. The reaction mixture was stirred at room temperatureovernight. The reaction mixture was then poured on top of a one-inchsilica gel plug, eluted with 30 mL of methylene chloride and the eluentwas rotary evaporated to yield 0.69 g of the amide (Compound 8), acompound of the invention. ¹H NMR (CDCl₃; 300 MHz) δ2.57 (s, 3H), 4.96(m, 2H), 7.22 (s, 1H), 7.48 (bs, 1H), 8.00 (s, 1H), 8.71 (s, 1H).

EXAMPLE 2 Preparation of2,4-Dichloro-N-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl]-3-pyridinecarboxamide

[0103] Step A: Preparation of 2,4-dichloropyridine

[0104] A solution of 6.7 g of 4-nitropyridine N-oxide in POCl₃ wasrefluxed for 3 hours and then cooled to room temperature. The solventwas removed under vacuum to leave an oily residue. Saturated sodiumbicarbonate solution (200 mL)was carefully added, followed by extractionwith methylene chloride (2×). The methylene chloride was then removedunder vacuum to provide an oil that was filtered through a plug ofsilica gel, eluting with 20% ethyl acetate in hexanes. Removal of thesolvent under vacuum left 1.6 g of an oil. ¹H NMR (CDCl₃; 300 MHz) δ7.25(d of d, 1H, J is 1.7, 5.4 Hz), 7.38 (d, 1H, J is 1.7 Hz), 8.31 (d, 1H,J is 5.4 Hz).

[0105] Step B: Preparation of 2,4-dichloro-3-pyridine Carboxaldehyde

[0106] Under nitrogen, a solution of 1.6 g of 2,4-dichloropyridine in 5mL dry tetrahydrofuran (THF) was added to a solution of 6 mL of lithiumdiisopropyl amide in 25 mL of THF at −70° C., followed by stirring atthis temperature for 3 hours. Then 1 mL of dry N,N-dimethylformamide wasadded at −70° C. followed by stirring at this temperature for 1 hour.Then 25 mL of saturated ammonium chloride solution was added and thereaction mixture was stirred at room temperature overnight. The reactionmixture was diluted with 25 mL of water and extracted with ethyl acetate(2×). The combine organic phases were distilled under vacuum to givesolids that were dissolved in 5 mL of methylene chloride and filteredthrough silica gel, eluting with 100% methylene chloride. Removal of thesolvent under vacuum provided the title intermediate as a solid. ¹H NMR(CDCl₃; 300 MHz) δ7.41 (d, 1H, J is 5.3 Hz), 8.42 (d, 1H, J is 5.2 Hz),10.5 (s, 1H).

[0107] Step C: Preparation of 2.4-dichloronicotinic Acid

[0108] A solution of 0.40 g of the aldehyde from Step B was dissolved in6 mL of THF and then added to a solution of 0.27 g of sodium chloriteand 0.29 g of sulfamic acid in 6 mL of water. The reaction mixture wasstirred at room temperature overnight. The reaction mixture was dilutedwith 1 N sodium hydroxide (10 mL) and extracted with diethyl ether (1×).The aqueous layer was then acidified with concentrated HCl, extractedwith methylene chloride (2×), and the combine methylene chlorideextracts were dried over magnesium sulfate. The methylene chloride wasremoved under vacuum to give 0.22 g of a solid. ¹H NMR (CDCl₃; 300 MHz)δ7.38 (d, 1H J is 5.4 Hz), 8.40 (d, 1H, J is 5.5 Hz), 8.60 (bs, 1H).

[0109] Step D: Preparation of2-Dichloro-N-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl]-3-pyridinecarboxamide

[0110] A solution of 0.22 g of the acid from Step C was refluxed inthionyl chloride for 1 hour followed by removal of the solvent undervacuum to give an oil. The oil was dissolved in 1 mL of methylenechloride and added to a solution of2-aminomethyl-3-chloro-5-trifluoromethylpyridine hydrochloride (0.25 g)and triethylamine (0.20 g) in 9 mL of methylene chloride at roomtemperature. The reaction mixture was stirred at room temperatureovernight. The reaction mixture was then filtered through silica gel,eluting with 100% methylene chloride. Removal of the solvent undervacuum provided the title compound as a solid, m.p. 122-124° C.

EXAMPLE 3 Preparation of2,4-Dichloro-N-[1-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl]-3-pyridinecarboxamide

[0111] Step A: Preparation of3-Chloro-α-methyl-5-(trifluoromethyl)-2-pyridinemethanamine

[0112] N-(diphenylmethylene)glycine ethyl ester (2.25 g) was added to asuspension of sodium hydride (0.74 g of 60% oil dispersion) in 20 mL ofdry N,N-dimethylformamide at room temperature, resulting in vigorous gasevolution. After stirring at room temperature for five minutes, 2 g of2,3-dichloro-5-trifluoromethylpyridine was added, followed by stirringat room temperature for 1 hour. Then 0.80 mL of methyl iodide was addedfollowed by stirring at room temperature overnight. The reaction mixturewas poured onto ice water, extracted with diethyl ether (2×), anddistilled under vacuum to remove the solvent leaving an oil. The oil wasthen refluxed in 6 NHCl overnight. The reaction mixture was cooled toroom temperature, made basic with solid sodium carbonate and extractedwith diethyl ether (2×). The combined extracts were dried over magnesiumsulfate and distilled under vacuum to remove the solvent, leaving 1.5 gof an oil. ¹H NMR (CDCl₃; 300 MHz) δ1.4 (d, 3H, J is 6.6 Hz), 4.6 (bs,1H), 7.88 (m, 1H), 8.75 (bs, 1H).

[0113] Step B: Preparation of2,4-Dichloro-N-[1-[3-chloro-5-trifluoromethyl)-2-pyridinyl]ethyl]-3-pyridinecarboxamide

[0114] 2,4-Dichloronicotinoyl chloride (0.40 g), made as in Example 1,Step C, was added to a solution of the amine intermediate from Step A(0.66 g) and triethylamine (0.70 g) in 30 mL of methylene chloride atroom temperature followed by stirring overnight. The reaction mixturewas distilled under vacuum to remove the solvent, giving an oil that wasfiltered through silica gel using 100% methylene chloride as the eluent.The solvent was then removed under vacuum to give the title compound, acompound of the invention, as a red oil.

[0115]¹H NMR (CDCl₃; 300 MHz) δ1.62 (d, 3H, J is 6.7 Hz), 5.48 (m, 1H),7.35 (d, 1H, J is 5.2 Hz), 7.40 (d, 1H, J is 6.9), 7.99 (d, 1H, J is 1.8Hz), 8.34 (d, 1H, J is 5.2), 8.70 (s, 1H).

EXAMPLE 4 Preparation of(+)-2,4-Dichloro-N-[1-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl]-3-pyridinecarboxamide

[0116] Step A: Resolution of3-Chloro-α-methyl-5-(trifluoromethyl)-2-pyridinemethanamine:

[0117] (−)-Menthyl chloroformate (0.92 g) was added to a solution of thealpha-methyl amine from Example 3, Step A (1 g) and triethylamine (1.2mL) in 25 mL of THF at room temperature followed by stirring at roomtemperature for 30 minutes. The solvent was then removed under vacuum togive an oil comprising two menthylcarbamate diastereomers that wereseparated via column chromatography (5% diethyl ether in hexanes aseluent) to give 0.20 g of the more polar diastereomer as an oil. Thisoil was then refluxed in 5 mL of trifluoroacetic acid for 4 hours tocleave the menthylcarbamate. The reaction mixture was allowed to cool toroom temperature and diluted with water (30 mL), made basic with solidsodium carbonate and extracted with methylene chloride. The organiclayer was dried over magnesium sulfate and distilled under vacuum togive 60 mg of the enantiomerically-enriched amine intermediate as anoil. ¹H NMR (CDCl₃; 300 MHz) δ1.41 (d, 3H, J is 6.7 Hz), 1.9 (bs, 2H),4.60 (m, 1H), 7.88 (m, 1H), 8.74 (s, 1H).

[0118] Step B: Preparation of(+)-2,4-Dichloro-N-[1-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl]-3-pyridinecarboxamide:

[0119] 2,4-Dichloronicotinoyl chloride (0.56 g), made as in Example 1,Step C was added to a solution of the enantiomerically-enriched aminefrom Step A (60 mg) and triethylamine (54 mg) in 10 mL of methylenechloride at room temperature followed by stirring overnight. Thereaction mixture was then filtered through silica gel using 100%methylene chloride as the eluent. The solvent was removed under vacuumto give the title compound, a compound of the invention, as a solid,m.p. 110-111° C. Polarimetric measurements of a solution ofapproximately 2 mg of the title compound in 1 mL of CDCl₃ rotates planepolarized light in the (+) or dextro direction.

[0120] The enantiomer of Example 4,(−)-2,4-Dichloro-N-[-1-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl]-3-pyridinecarboxamide,was prepared in analogoous fashion using3-chloro-α-methyl-5-(trifluoromethyl)-2-pyridinemethanamine that hasbeen enriched in the opposite enantiomer from that obtained in Example4, Step A.

EXAMPLE 5 Preparation ofN-[1-(5-bromo-3-chloro-2-pyridinyl)ethyl]-2,4-dichloro-3-pyridinecarboxamide

[0121] Step A: Preparation of 5-bromo-3-chloro-2 (1)-pyridone

[0122] A solution of 6.2 g of potassium chlorate in 100 mL of water wasadded to a solution of 25 g of 5-bromo-2-pyridone in 100 mL concentratedHCl pre-heated to 50° C. to 60° C. to form a thick precipitate that wasstirred for 5 min. Then, 60 mL of water was added to facilitate stirringand the mixture was stirred at room temperature overnight. The reactionmixture was filtered, triturated with water (2×), and the precipitatesuction-dried to yield 17.7 g of the desired intermediate as a solid.NMR (CDCl₃, 300 MHz): δ7.53 (d, 1H, J is 2.6 Hz), 7.75 (d, 1H, J is 2.5Hz)

[0123] Step B: Preparation of 5-bromo-2,3-dichloropyridine

[0124] The product of Step A (17.7 g) and 10 g of PCl₅ were combinedinto 100 mL POCl₃, and the mixture was refluxed for 4 hours withscrubbing. The reaction mixture was concentrated under reduced pressureto remove most of the POCl₃, carefully poured into warm water, cooled toroom temperature and then extracted with methylene chloride (2×). Thecombined extracts were dried over magnesium sulfate and concentrated togive an oil which was subjected to column chromatography(8:2/hexanes:EtOAc) to give 4.2 g of the desired intermediate as an oil.NMR (CDCl₃; 300 MHz): δ7.94 (d, 1H, J is 2.2 Hz), 8.37 (d, 1H, J is 2.3Hz).

[0125] Step C: Preparation of5-Bromo-3-chloro-α-methyl-2-pyridinemethanamine Hydrochloride

[0126] Under nitrogen, 4.1 g of the title compound from Step B was addedto a suspension of sodium hydride (60% oil suspension) in 30 mL of dryN,N-dimethylformamide, cooled to 0° C. N-(Diphenylmethylene)glycineethyl ester (4.6 g) was added in portions with no exotherm, and themixture was stirred at room temperature for 3 hours. Then, 3.4 mL ofmethyl iodide was added at <30° C. and the reaction mixture was stirredovernight at room temperature. The reaction mixture was diluted withwater and extracted with diethyl ether (2×). The combined extracts werewashed with saturated brine (1×) and reduced in vacuo to an oil that wasthen refluxed in 50 mL of 12N HCl for 4 hours. The reaction mixture wasreduced in vacuo to an oil, cooled, and slurried with diethyl etherovernight. The ether was then decanted off and the residue was dried ina vacuum oven to give 1.3 g of the desired intermediate as a solid.NMR(CDCl₃; 300 MHz): 1.40 and 1.46 (2 doublets, 3H, J is 7.0 Hz), 4.7(m, 1H), 8.48 (d, 1H, J is 1.8), 8.6 (bs, 3H), 8.79 (d, 1H, J is 1.9Hz).

[0127] Step D: Preparation ofN-[1-(5-bromo-3-chloro-2-pyridinyl)ethyl]-2,4-dichloro-3-pyridinecarboxamide

[0128] The product of Step C (0.80 g), 1.21 mL of triethyl amine and0.62 g of 2,4-dichloronicotinoyl chloride were combined in that order at<20° C. in 25 mL of methylene chloride, and the mixture was stirred atroom temperature overnight. The reaction mixture was reduced in vacuo toproduce the title compound, a compound of the invention, as a solid. NMR(CDCl₃; 300 MHz): δ1.59 (d, 3H, J is 6.6 Hz), 5.75 (m, 1H), 7.3 (bs,1H), 7.34 (d, 1H, J is 5.2 Hz), 7.91 (d, 1H, J is 1.9 Hz), 8.33 (d, 1H,J is 5.4 Hz), 8.49 (d, 1H, J is 1.9 Hz).

EXAMPLE 6 Preparation of2,4-Dichloro-N-[1-3,5-dichloro-2-pyridinyl)ethyl]-3-pyridinecarboxamide

[0129] Example 6 was prepared in analogous fashion to Example 5 using2-bromo-3,5-dichloropyridine as the staring material and subjecting thismaterial to conditions analogous to those described in Steps C (toprepare 3,5-dichloro-α-methyl-2-pyridinemethanamine) and D of Example 5to give the title compound, a compound of the invention, as a solid. NMR(CDCl₃; 300 MHz): δ1.58 (d, 3H, J is 6.6 Hz), 5.7-5.8 (m, 1H), 7.4 (m,2H), 7.77 (m, 1H), 8.35 (m, 1H), 8.40 (m, 1H).

[0130] By the procedures described herein together with methods known inthe art, the following compounds of Tables 1-9 can be prepared. Thefollowing abbreviations are used in the Tables which follow: t istertiary, s is secondary, n is normal, i is iso, c is cyclo, Me ismethyl, Et is ethyl, Pr is propyl, i-Pr is isopropyl, Bu is butyl, Ph isphenyl, OMe is methoxy, OEt is ethoxy, SMe is methylthio, SEt isethylthio, CN is cyano, NO₂ is nitro, TMS is trimethylsilyl, S(O)Me ismethylsulfinyl, and S(O)₂Me is methylsulfonyl. The substituents M, Q andR are equivalent to independent R⁵ substituents that have been locatedin the positions indicated. The substituents T, U and V are equivalentto independent R⁶ substituents that have been located in the positionsindicated. TABLE 1

T U V T U V Me Me Me Br Me Me Me Me F Br Me F Me Me Cl Br Me Cl Me Me BrBr Me Br Me Me CF₃ Br Me CF₃ Me Me NO₂ Br Me NO₂ Me Me OMe Br Me OMe FMe Me CF₃ Me Me F Me F CF₃ Me F F Me Cl CF₃ Me Cl F Me Br CF₃ Me Br F MeCF₃ CF₃ Me CF₃ F Me NO₂ CF₃ Me NO₂ F Me OMe CF₃ Me OMe Cl Me Me NO₂ MeMe Cl Me F NO₂ Me F Cl Me Cl NO₂ Me Cl Cl Me Br NO₂ Me Br Cl Me CF₃ NO₂Me CF₃ Cl Me NO₂ NO₂ Me NO₂ Cl Me OMe NO₂ Me OMe Me F Me Br F Me Me F FBr F F Me F Cl Br F Cl Me F Br Br F Br Me F CF₃ Br F CF₃ Me F NO₂ Br FNO₂ Me F OMe Br F OMe F F Me CF₃ F Me F F F CF₃ F F F F Cl CF₃ F Cl F FBr CF₃ F Br F F CF₃ CF₃ F CF₃ F F NO₂ CF₃ F NO₂ F F OMe CF₃ F OMe Cl FMe NO₂ F Me Cl F F NO₂ F F Cl F Cl NO₂ F Cl Cl F Br NO₂ F Br Cl F CF₃NO₂ F CF₃ Cl F NO₂ NO₂ F NO₂ Cl F OMe NO₂ F OMe Me Cl Me Br Cl Me Me ClF Br Cl F Me Cl Cl Br Cl Cl Me Cl Br Br Cl Br Me Cl CF₃ Br Cl CF₃ Me ClNO₂ Br Cl NO₂ Me Cl OMe Br Cl OMe F Cl Me CF₃ Cl Me F Cl F CF₃ Cl F F ClCl CF₃ Cl Cl F Cl Br CF₃ Cl Br F Cl CF₃ CF₃ Cl CF₃ F Cl NO₂ CF₃ Cl NO₂ FCl OMe CF₃ Cl OMe Cl Cl Me NO₂ Cl Me Cl Cl F NO₂ Cl F Cl Cl Cl NO₂ Cl ClCl Cl Br NO₂ Cl Br Cl Cl CF₃ NO₂ Cl CF₃ Cl Cl NO₂ NO₂ Cl NO₂ Cl Cl OMeNO₂ Cl OMe Me Br Me Br Br Me Me Br F Br Br F Me Br Cl Br Br Cl Me Br BrBr Br Br Me Br CF₃ Br Br CF₃ Me Br NO₂ Br Br NO₂ Me Br OMe Br Br OMe FBr Me CF₃ Br Me F Br F CF₃ Br F F Br Cl CF₃ Br Cl F Br Br CF₃ Br Br F BrCF₃ CF₃ Br CF₃ F Br NO₂ CF₃ Br NO₂ F Br OMe CF₃ Br OMe Cl Br Me NO₂ BrMe Cl Br F NO₂ Br F Cl Br Cl NO₂ Br Cl Cl Br Br NO₂ Br Br Cl Br CF₃ NO₂Br CF₃ Cl Br NO₂ NO₂ Br NO₂ Cl Br OMe NO₂ Br OMe Me CF₃ Me Br CF₃ Me MeCF₃ F Br CF₃ F Me CF₃ Cl Br CF₃ Cl Me CF₃ Br Br CF₃ Br Me CF₃ CF₃ Br CF₃CF₃ Me CF₃ NO₂ Br CF₃ NO₂ Me CF₃ OMe Br CF₃ OMe F CF₃ Me CF₃ CF₃ Me FCF₃ F CF₃ CF₃ F F CF₃ Cl CF₃ CF₃ Cl F CF₃ Br CF₃ CF₃ Br F CF₃ CF₃ CF₃CF₃ CF₃ F CF₃ NO₂ CF₃ CF₃ NO₂ F CF₃ OMe CF₃ CF₃ OMe Cl CF₃ Me NO₂ CF₃ MeCl CF₃ F NO₂ CF₃ F Cl CF₃ Cl NO₂ CF₃ Cl Cl CF₃ Br NO₂ CF₃ Br Cl CF₃ CF₃NO₂ CF₃ CF₃ Cl CF₃ NO₂ NO₂ CF₃ NO₂ Cl CF₃ OMe NO₂ CF₃ OMe Me NO₂ Me BrNO₂ Me Me NO₂ F Br NO₂ F Me NO₂ Cl Br NO₂ Cl Me NO₂ Br Br NO₂ Br Me NO₂CF₃ Br NO₂ CF₃ Me NO₂ NO₂ Br NO₂ NO₂ Me NO₂ OMe Br NO₂ OMe F NO₂ Me CF₃NO₂ Me F NO₂ F CF₃ NO₂ F F NO₂ Cl CF₃ NO₂ Cl F NO₂ Br CF₃ NO₂ Br F NO₂CF₃ CF₃ NO₂ CF₃ F NO₂ NO₂ CF₃ NO₂ NO₂ F NO₂ OMe CF₃ NO₂ OMe Cl NO₂ MeNO₂ NO₂ Me Cl NO₂ F NO₂ NO₂ F Cl NO₂ Cl NO₂ NO₂ Cl Cl NO₂ Br NO₂ NO₂ BrCl NO₂ CF₃ NO₂ NO₂ CF₃ Cl NO₂ NO₂ NO₂ NO₂ NO₂ Cl NO₂ OMe NO₂ NO₂ OMe MeOMe Me Br OMe Me Me OMe F Br OMe F Me OMe Cl Br OMe Cl Me OMe Br Br OMeBr Me OMe CF₃ Br OMe CF₃ Me OMe NO₂ Br OMe NO₂ Me OMe OMe Br OMe OMe FOMe Me CF₃ OMe Me F OMe F CF₃ OMe F F OMe Cl CF₃ OMe Cl F OMe Br CF₃ OMeBr F OMe CF₃ CF₃ OMe CF₃ F OMe NO₂ CF₃ OMe NO₂ F OMe OMe CF₃ OMe OMe ClOMe Me NO₂ OMe Me Cl OMe F NO₂ OMe F Cl OMe Cl NO₂ OMe Cl Cl OMe Br NO₂OMe Br Cl OMe CF₃ NO₂ OMe CF₃ Cl OMe NO₂ NO₂ OMe NO₂ Cl OMe OMe NO₂ OMeOMe Me H Me Br H Me Me H F Br H F Me H Cl Br H Cl Me H Br Br H Br Me HCF₃ Br H CF₃ Me H NO₂ Br H NO₂ Me H OMe Br H OMe F H Me CF₃ H Me F H FCF₃ H F F H Cl CF₃ H Cl F H Br CF₃ H Br F H CF₃ CF₃ H CF₃ F H NO₂ CF₃ HNO₂ F H OMe CF₃ H OMe Cl H Me NO₂ H Me Cl H F NO₂ H F Cl H Cl NO₂ H ClCl H Br NO₂ H Br Cl H CF₃ NO₂ H CF₃ Cl H NO₂ NO₂ H NO₂ Cl H OMe NO₂ HOMe OMe Me Me OMe Br Me OMe Me F OMe Br F OMe Me Cl OMe Br Cl OMe Me BrOMe Br Br OMe Me CF₃ OMe Br CF₃ OMe Me NO₂ OMe Br NO₂ OMe Me OMe OMe BrOMe OMe F Me OMe CF₃ Me OMe F F OMe CF₃ F OMe F Cl OMe CF₃ Cl OMe F BrOMe CF₃ Br OMe F CF₃ OMe CF₃ CF₃ OMe F NO₂ OMe CF₃ NO₂ OMe F OMe OMe CF₃OMe OMe Cl Me OMe NO₂ Me OMe Cl F OMe NO₂ F OMe Cl Cl OMe NO₂ Cl OMe ClBr OMe NO₂ Br OMe Cl CF₃ OMe NO₂ CF₃ OMe Cl NO₂ OMe NO₂ NO₂ OMe Cl OMeOMe NO₂ OMe OMe H Me OMe H Br OMe H F OMe H CF₃ OMe H Cl OMe H NO₂ OMe HOMe OMe OMe Me OMe OMe CF₃ OMe OMe F OMe OMe NO₂ OMe OMe Cl OMe OMe OMeOMe OMe Br

[0131] TABLE 2

T U V T U V Me Me Me Br Me Me Me Me F Br Me F Me Me Cl Br Me Cl Me Me BrBr Me Br Me Me CF₃ Br Me CF₃ Me Me NO₂ Br Me NO₂ Me Me OMe Br Me OMe FMe Me CF₃ Me Me F Me F CF₃ Me F F Me Cl CF₃ Me Cl F Me Br CF₃ Me Br F MeCF₃ CF₃ Me CF₃ F Me NO₂ CF₃ Me NO₂ F Me OMe CF₃ Me OMe Cl Me Me NO₂ MeMe Cl Me F NO₂ Me F Cl Me Cl NO₂ Me Cl Cl Me Br NO₂ Me Br Cl Me CF₃ NO₂Me CF₃ Cl Me NO₂ NO₂ Me NO₂ Cl Me OMe NO₂ Me OMe Me F Me Br F Me Me F FBr F F Me F Cl Br F Cl Me F Br Br F Br Me F CF₃ Br F CF₃ Me F NO₂ Br FNO₂ Me F OMe Br F OMe F F Me CF₃ F Me F F F CF₃ F F F F Cl CF₃ F Cl F FBr CF₃ F Br F F CF₃ CF₃ F CF₃ F F NO₂ CF₃ F NO₂ F F OMe CF₃ F OMe Cl FMe NO₂ F Me Cl F F NO₂ F F Cl F Cl NO₂ F Cl Cl F Br NO₂ F Br Cl F CF₃NO₂ F CF₃ Cl F NO₂ NO₂ F NO₂ Cl F OMe NO₂ F OMe Me Cl Me Br Cl Me Me ClF Br Cl F Me Cl Cl Br Cl Cl Me Cl Br Br Cl Br Me Cl CF₃ Br Cl CF₃ Me ClNO₂ Br Cl NO₂ Me Cl OMe Br Cl OMe F Cl Me CF₃ Cl Me F Cl F CF₃ Cl F F ClCl CF₃ Cl Cl F Cl Br CF₃ Cl Br F Cl CF₃ CF₃ Cl CF₃ F Cl NO₂ CF₃ Cl NO₂ FCl OMe CF₃ Cl OMe Cl Cl Me NO₂ Cl Me Cl Cl F NO₂ Cl F Cl Cl Cl NO₂ Cl ClCl Cl Br NO₂ Cl Br Cl Cl CF₃ NO₂ Cl CF₃ Cl Cl NO₂ NO₂ Cl NO₂ Cl Cl OMeNO₂ Cl OMe Me Br Me Br Br Me Me Br F Br Br F Me Br Cl Br Br Cl Me Br BrBr Br Br Me Br CF₃ Br Br CF₃ Me Br NO₂ Br Br NO₂ Me Br OMe Br Br OMe FBr Me CF₃ Br Me F Br F CF₃ Br F F Br Cl CF₃ Br Cl F Br Br CF₃ Br Br F BrCF₃ CF₃ Br CF₃ F Br NO₂ CF₃ Br NO₂ F Br OMe CF₃ Br OMe Cl Br Me NO₂ BrMe Cl Br F NO₂ Br F Cl Br Cl NO₂ Br Cl Cl Br Br NO₂ Br Br Cl Br CF₃ NO₂Br CF₃ Cl Br NO₂ NO₂ Br NO₂ Cl Br OMe NO₂ Br OMe Me CF₃ Me Br CF₃ Me MeCF₃ F Br CF₃ F Me CF₃ Cl Br CF₃ Cl Me CF₃ Br Br CF₃ Br Me CF₃ CF₃ Br CF₃CF₃ Me CF₃ NO₂ Br CF₃ NO₂ Me CF₃ OMe Br CF₃ OMe F CF₃ Me CF₃ CF₃ Me FCF₃ F CF₃ CF₃ F F CF₃ Cl CF₃ CF₃ Cl F CF₃ Br CF₃ CF₃ Br F CF₃ CF₃ CF₃CF₃ CF₃ F CF₃ NO₂ CF₃ CF₃ NO₂ F CF₃ OMe CF₃ CF₃ OMe Cl CF₃ Me NO₂ CF₃ MeCl CF₃ F NO₂ CF₃ F Cl CF₃ Cl NO₂ CF₃ Cl Cl CF₃ Br NO₂ CF₃ Br Cl CF₃ CF₃NO₂ CF₃ CF₃ Cl CF₃ NO₂ NO₂ CF₃ NO₂ Cl CF₃ OMe NO₂ CF₃ OMe Me NO₂ Me BrNO₂ Me Me NO₂ F Br NO₂ F Me NO₂ Cl Br NO₂ Cl Me NO₂ Br Br NO₂ Br Me NO₂CF₃ Br NO₂ CF₃ Me NO₂ NO₂ Br NO₂ NO₂ Me NO₂ OMe Br NO₂ OMe F NO₂ Me CF₃NO₂ Me F NO₂ F CF₃ NO₂ F F NO₂ Cl CF₃ NO₂ Cl F NO₂ Br CF₃ NO₂ Br F NO₂CF₃ CF₃ NO₂ CF₃ F NO₂ NO₂ CF₃ NO₂ NO₂ F NO₂ OMe CF₃ NO₂ OMe Cl NO₂ MeNO₂ NO₂ Me Cl NO₂ F NO₂ NO₂ F Cl NO₂ Cl NO₂ NO₂ Cl Cl NO₂ Br NO₂ NO₂ BrCl NO₂ CF₃ NO₂ NO₂ CF₃ Cl NO₂ NO₂ NO₂ NO₂ NO₂ Cl NO₂ OMe NO₂ NO₂ OMe MeOMe Me Br OMe Me Me OMe F Br OMe F Me OMe Cl Br OMe Cl Me OMe Br Br OMeBr Me OMe CF₃ Br OMe CF₃ Me OMe NO₂ Br OMe NO₂ Me OMe OMe Br OMe OMe FOMe Me CF₃ OMe Me F OMe F CF₃ OMe F F OMe Cl CF₃ OMe Cl F OMe Br CF₃ OMeBr F OMe CF₃ CF₃ OMe CF₃ F OMe NO₂ CF₃ OMe NO₂ F OMe OMe CF₃ OMe OMe ClOMe Me NO₂ OMe Me Cl OMe F NO₂ OMe F Cl OMe Cl NO₂ OMe Cl Cl OMe Br NO₂OMe Br Cl OMe CF₃ NO₂ OMe CF₃ Cl OMe NO₂ NO₂ OMe NO₂ Cl OMe OMe NO₂ OMeOMe Me H Me Br H Me Me H F Br H F Me H Cl Br H Cl Me H Br Br H Br Me HCF₃ Br H CF₃ Me H NO₂ Br H NO₂ Me H OMe Br H OMe F H Me CF₃ H Me F H FCF₃ H F F H Cl CF₃ H Cl F H Br CF₃ H Br F H CF₃ CF₃ H CF₃ F H NO₂ CF₃ HNO₂ F H OMe CF₃ H OMe Cl H Me NO₂ H Me Cl H F NO₂ H F Cl H Cl NO₂ H ClCl H Br NO₂ H Br Cl H CF₃ NO₂ H CF₃ Cl H NO₂ NO₂ H NO₂ Cl H OMe NO₂ HOMe OMe Me Me OMe Br Me OMe Me F OMe Br F OMe Me Cl OMe Br Cl OMe Me BrOMe Br Br OMe Me CF₃ OMe Br CF₃ OMe Me NO₂ OMe Br NO₂ OMe Me OMe OMe BrOMe OMe F Me OMe CF₃ Me OMe F F OMe CF₃ F OMe F Cl OMe CF₃ Cl OMe F BrOMe CF₃ Br OMe F CF₃ OMe CF₃ CF₃ OMe F NO₂ OMe CF₃ NO₂ OMe F OMe OMe CF₃OMe OMe Cl Me OMe NO₂ Me OMe Cl F OMe NO₂ F OMe Cl Cl OMe NO₂ Cl OMe ClBr OMe NO₂ Br OMe Cl CF₃ OMe NO₂ CF₃ OMe Cl NO₂ OMe NO₂ NO₂ OMe Cl OMeOMe NO₂ OMe OMe H Me OMe H Br OMe H F OMe H CF₃ OMe H Cl OMe H NO₂ OMe HOMe OMe OMe Me OMe OMe CF₃ OMe OMe F OMe OMe NO₂ OMe OMe Cl OMe OMe OMeOMe OMe Br

[0132] TABLE 3

T U V T U V Me Me Me Br Me Me Me Me F Br Me F Me Me Cl Br Me Cl Me Me BrBr Me Br Me Me CF₃ Br Me CF₃ Me Me NO₂ Br Me NO₂ Me Me OMe Br Me OMe FMe Me CF₃ Me Me F Me F CF₃ Me F F Me Cl CF₃ Me Cl F Me Br CF₃ Me Br F MeCF₃ CF₃ Me CF₃ F Me NO₂ CF₃ Me NO₂ F Me OMe CF₃ Me OMe Cl Me Me NO₂ MeMe Cl Me F NO₂ Me F Cl Me Cl NO₂ Me Cl Cl Me Br NO₂ Me Br Cl Me CF₃ NO₂Me CF₃ Cl Me NO₂ NO₂ Me NO₂ Cl Me OMe NO₂ Me OMe Me F Me Br F Me Me F FBr F F Me F Cl Br F Cl Me F Br Br F Br Me F CF₃ Br F CF₃ Me F NO₂ Br FNO₂ Me F OMe Br F OMe F F Me CF₃ F Me F F F CF₃ F F F F Cl CF₃ F Cl F FBr CF₃ F Br F F CF₃ CF₃ F CF₃ F F NO₂ CF₃ F NO₂ F F OMe CF₃ F OMe Cl FMe NO₂ F Me Cl F F NO₂ F F Cl F Cl NO₂ F Cl Cl F Br NO₂ F Br Cl F CF₃NO₂ F CF₃ Cl F NO₂ NO₂ F NO₂ Cl F OMe NO₂ F OMe Me Cl Me Br Cl Me Me ClF Br Cl F Me Cl Cl Br Cl Cl Me Cl Br Br Cl Br Me Cl CF₃ Br Cl CF₃ Me ClNO₂ Br Cl NO₂ Me Cl OMe Br Cl OMe F Cl Me CF₃ Cl Me F Cl F CF₃ Cl F F ClCl CF₃ Cl Cl F Cl Br CF₃ Cl Br F Cl CF₃ CF₃ Cl CF₃ F Cl NO₂ CF₃ Cl NO₂ FCl OMe CF₃ Cl OMe Cl Cl Me NO₂ Cl Me Cl Cl F NO₂ Cl F Cl Cl Cl NO₂ Cl ClCl Cl Br NO₂ Cl Br Cl Cl CF₃ NO₂ Cl CF₃ Cl Cl NO₂ NO₂ Cl NO₂ Cl Cl OMeNO₂ Cl OMe Me Br Me Br Br Me Me Br F Br Br F Me Br Cl Br Br Cl Me Br BrBr Br Br Me Br CF₃ Br Br CF₃ Me Br NO₂ Br Br NO₂ Me Br OMe Br Br OMe FBr Me CF₃ Br Me F Br F CF₃ Br F F Br Cl CF₃ Br Cl F Br Br CF₃ Br Br F BrCF₃ CF₃ Br CF₃ F Br NO₂ CF₃ Br NO₂ F Br OMe CF₃ Br OMe Cl Br Me NO₂ BrMe Cl Br F NO₂ Br F Cl Br Cl NO₂ Br Cl Cl Br Br NO₂ Br Br Cl Br CF₃ NO₂Br CF₃ Cl Br NO₂ NO₂ Br NO₂ Cl Br OMe NO₂ Br OMe Me CF₃ Me Br CF₃ Me MeCF₃ F Br CF₃ F Me CF₃ Cl Br CF₃ Cl Me CF₃ Br Br CF₃ Br Me CF₃ CF₃ Br CF₃CF₃ Me CF₃ NO₂ Br CF₃ NO₂ Me CF₃ OMe Br CF₃ OMe F CF₃ Me CF₃ CF₃ Me FCF₃ F CF₃ CF₃ F F CF₃ Cl CF₃ CF₃ Cl F CF₃ Br CF₃ CF₃ Br F CF₃ CF₃ CF₃CF₃ CF₃ F CF₃ NO₂ CF₃ CF₃ NO₂ F CF₃ OMe CF₃ CF₃ OMe Cl CF₃ Me NO₂ CF₃ MeCl CF₃ F NO₂ CF₃ F Cl CF₃ Cl NO₂ CF₃ Cl Cl CF₃ Br NO₂ CF₃ Br Cl CF₃ CF₃NO₂ CF₃ CF₃ Cl CF₃ NO₂ NO₂ CF₃ NO₂ Cl CF₃ OMe NO₂ CF₃ OMe Me NO₂ Me BrNO₂ Me Me NO₂ F Br NO₂ F Me NO₂ Cl Br NO₂ Cl Me NO₂ Br Br NO₂ Br Me NO₂CF₃ Br NO₂ CF₃ Me NO₂ NO₂ Br NO₂ NO₂ Me NO₂ OMe Br NO₂ OMe F NO₂ Me CF₃NO₂ Me F NO₂ F CF₃ NO₂ F F NO₂ Cl CF₃ NO₂ Cl F NO₂ Br CF₃ NO₂ Br F NO₂CF₃ CF₃ NO₂ CF₃ F NO₂ NO₂ CF₃ NO₂ NO₂ F NO₂ OMe CF₃ NO₂ OMe Cl NO₂ MeNO₂ NO₂ Me Cl NO₂ F NO₂ NO₂ F Cl NO₂ Cl NO₂ NO₂ Cl Cl NO₂ Br NO₂ NO₂ BrCl NO₂ CF₃ NO₂ NO₂ CF₃ Cl NO₂ NO₂ NO₂ NO₂ NO₂ Cl NO₂ OMe NO₂ NO₂ OMe MeOMe Me Br OMe Me Me OMe F Br OMe F Me OMe Cl Br OMe Cl Me OMe Br Br OMeBr Me OMe CF₃ Br OMe CF₃ Me OMe NO₂ Br OMe NO₂ Me OMe OMe Br OMe OMe FOMe Me CF₃ OMe Me F OMe F CF₃ OMe F F OMe Cl CF₃ OMe Cl F OMe Br CF₃ OMeBr F OMe CF₃ CF₃ OMe CF₃ F OMe NO₂ CF₃ OMe NO₂ F OMe OMe CF₃ OMe OMe ClOMe Me NO₂ OMe Me Cl OMe F NO₂ OMe F Cl OMe Cl NO₂ OMe Cl Cl OMe Br NO₂OMe Br Cl OMe CF₃ NO₂ OMe CF₃ Cl OMe NO₂ NO₂ OMe NO₂ Cl OMe OMe NO₂ OMeOMe Me H Me Br H Me Me H F Br H F Me H Cl Br H Cl Me H Br Br H Br Me HCF₃ Br H CF₃ Me H NO₂ Br H NO₂ Me H OMe Br H OMe F H Me CF₃ H Me F H FCF₃ H F F H Cl CF₃ H Cl F H Br CF₃ H Br F H CF₃ CF₃ H CF₃ F H NO₂ CF₃ HNO₂ F H OMe CF₃ H OMe Cl H Me NO₂ H Me Cl H F NO₂ H F Cl H Cl NO₂ H ClCl H Br NO₂ H Br Cl H CF₃ NO₂ H CF₃ Cl H NO₂ NO₂ H NO₂ Cl H OMe NO₂ HOMe OMe Me Me OMe Br Me OMe Me F OMe Br F OMe Me Cl OMe Br Cl OMe Me BrOMe Br Br OMe Me CF₃ OMe Br CF₃ OMe Me NO₂ OMe Br NO₂ OMe Me OMe OMe BrOMe OMe F Me OMe CF₃ Me OMe F F OMe CF₃ F OMe F Cl OMe CF₃ Cl OMe F BrOMe CF₃ Br OMe F CF₃ OMe CF₃ CF₃ OMe F NO₂ OMe CF₃ NO₂ OMe F OMe OMe CF₃OMe OMe Cl Me OMe NO₂ Me OMe Cl F OMe NO₂ F OMe Cl Cl OMe NO₂ Cl OMe ClBr OMe NO₂ Br OMe Cl CF₃ OMe NO₂ CF₃ OMe Cl NO₂ OMe NO₂ NO₂ OMe Cl OMeOMe NO₂ OMe OMe H Me OMe H Br OMe H F OMe H CF₃ OMe H Cl OMe H NO₂ OMe HOMe OMe OMe Me OMe OMe CF₃ OMe OMe F OMe OMe NO₂ OMe OMe Cl OMe OMe OMeOMe OMe Br

[0133] TABLE 4

T and V are both Cl and U is H Q R M Q R M Cl Cl H Cl Cl Me Cl Br H ClBr Me Cl OCF₃ H Cl OCF₃ Me Cl OCHF₂ H Cl OCHF₂ Me Cl OCH₂CF₃ H ClOCH₂CF₃ Me Cl OCF₂CF₃ H Cl OCF₂CF₃ Me Cl OCF₂CF₂H H Cl OCF₂CF₂H Me ClOCHFCF₃ H Cl OCHFCF₃ Me Cl SCF₃ H Cl SCF₃ Me Cl SCHF₂ H Cl SCHF₂ Me ClSCH₂CF₃ H Cl SCH₂CF₃ Me Cl SCF₂CF₃ H Cl SCF₂CF₃ Me Cl SCF₂CF₂H H ClSCF₂CF₂H Me Cl SCHFCF₃ H Cl SCHFCF₃ Me Cl SOCF₃ H Cl SOCF₃ Me Cl SOCHF₂H Cl SOCHF₂ Me Cl SOCH₂CF₃ H Cl SOCH₂CF₃ Me Cl SOCF₂CF₃ H Cl SOCF₂CF₃ MeCl SOCF₂CF₂H H Cl SOCF₂CF₂H Me Cl SOCHFCF₃ H Cl SOCHFCF₃ Me Cl SO₂CF₃ HCl SO₂CF₃ Me Cl SO₂CHF₂ H Cl SO₂CHF₂ Me Cl SO₂CH₂CF₃ H Cl SO₂CH₂CF₃ MeCl SO₂CF₂CF₃ H Cl SO₂CF₂CF₃ Me Cl SO₂CF₂CF₂H H Cl SO₂CF₂CF₂H Me ClSO₂CHFCF₃ H Cl SO₂CHFCF₃ Me Cl CN H Cl CN Me Br Cl H Br Cl Me Br Br H BrBr Me Br OCF₃ H Br OCF₃ Me Br OCHF₂ H Br OCHF₂ Me Br OCH₂CF₃ H BrOCH₂CF₃ Me Br OCF₂CF₃ H Br OCF₂CF₃ Me Br OCF₂CF₂H H Br OCF₂CF₂H Me BrOCHFCF₃ H Br OCHFCF₃ Me Br SCF₃ H Br SCF₃ Me Br SCHF₂ H Br SCHF₂ Me BrSCH₂CF₃ H Br SCH₂CF₃ Me Br SCF₂CF₃ H Br SCF₂CF₃ Me Br SCF₂CF₂H H BrSCF₂CF₂H Me Br SCHFCF₃ H Br SCHFCF₃ Me Br SOCF₃ H Br SOCF₃ Me Br SOCHF₂H Br SOCHF₂ Me Br SOCH₂CF₃ H Br SOCH₂CF₃ Me Br SOCF₂CF₃ H Br SOCF₂CF₃ MeBr SOCF₂CF₂H H Br SOCF₂CF₂H Me Br SOCHFCF₃ H Br SOCHFCF₃ Me Br SO₂CF₃ HBr SO₂CF₃ Me Br SO₂CHF₂ H Br SO₂CHF₂ Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃ MeBr SO₂CF₂CF₃ H Br SO₂CF₂CF₃ Me Br SO₂CF₂CF₂H H Br SO₂CF₂CF₂H Me BrSO₂CHFCF₃ H Br SO₂CHFCF₃ Me Br CN H Br CN Me T and V are both Cl and Uis Me Q R S Q R S Cl Cl H Cl Cl Me Cl Br H Cl Br Me Cl OCF₃ H Cl OCF₃ MeCl OCHF₂ H Cl OCHF₂ Me Cl OCH₂CF₃ H Cl OCH₂CF₃ Me Cl OCF₂CF₃ H ClOCF₂CF₃ Me Cl OCF₂CF₂H H Cl OCF₂CF₂H Me Cl OCHFCF₃ H Cl OCHFCF₃ Me ClSCF₃ H Cl SCF₃ Me Cl SCHF₂ H Cl SCHF₂ Me Cl SCH₂CF₃ H Cl SCH₂CF₃ Me ClSCF₂CF₃ H Cl SCF₂CF₃ Me Cl SCF₂CF₂H H Cl SCF₂CF₂H Me Cl SCHFCF₃ H ClSCHFCF₃ Me Cl SOCF₃ H Cl SOCF₃ Me Cl SOCHF₂ H Cl SOCHF₂ Me Cl SOCH₂CF₃ HCl SOCH₂CF₃ Me Cl SOCF₂CF₃ H Cl SOCF₂CF₃ Me Cl SOCF₂CF₂H H Cl SOCF₂CF₂HMe Cl SOCHFCF₃ H Cl SOCHFCF₃ Me Cl SO₂CF₃ H Cl SO₂CF₃ Me Cl SO₂C₂ H ClSO₂CH₂ Me Cl SO₂CH₂CF₃ H Cl SO₂CH₂CF₃ Me Cl SO₂CF₂CF₃ H Cl SO₂CF₂CF₃ MeCl SO₂CF₂CF₂H H Cl SO₂CF₂CF₂H Me Cl SO₂CHFCF₃ H Cl SO₂CHFCF₃ Me Cl CN HCl CN Me Br Cl H Br Cl Me Br Br H Br Br Me Br OCF₃ H Br OCF₃ Me Br OCHF₂H Br OCHF₂ Me Br OCH₂CF₃ H Br OCH₂CF₃ Me Br OCF₂CF₃ H Br OCF₂CF₃ Me BrOCF₂CF₂H H Br OCF₂CF₂H Me Br OCHFCF₃ H Br OCHFCF₃ Me Br SCF₃ H Br SCF₃Me Br SCHF₂ H Br SCHF₂ Me Br SCH₂CF₃ H Br SCH₂CF₃ Me Br SCF₂CF₃ H BrSCF₂CF₃ Me Br SCF₂CF₂H H Br SCF₂CF₂H Me Br SCHFCF₃ H Br SCHFCF₃ Me BrSOCF₃ H Br SOCF₃ Me Br SOCHF₂ H Br SOCHF₂ Me Br SOCH₂CF₃ H Br SOCH₂CF₃Me Br SOCF₂CF₃ H Br SOCF₂CF₃ Me Br SOCF₂CF₂H H Br SOCF₂CF₂H Me BrSOCHFCF₃ H Br SOCHFCF₃ Me Br SO₂CF₃ H Br SO₂CF₃ Me Br SO₂CHF₂ H BrSO₂CHF₂ Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃ Me Br SO₂CF₂CF₃ H Br SO₂CF₂CF₃ MeBr SO₂CF₂CF₂H H Br SO₂CF₂CF₂H Me Br SO₂CHFCF₃ H Br SO₂CHFCF₃ Me Br CN HBr CN Me T is Cl and V and U are both Me Cl Cl H Cl Cl Me Cl Br H Cl BrMe Cl OCF₃ H Cl OCF₃ Me Cl OCHF₂ H Cl OCHF₂ Me Cl OCH₂CF₃ H Cl OCH₂CF₃Me Cl OCF₂CF₃ H Cl OCF₂CF₃ Me Cl OCF₂CF₂H H Cl OCF₂CF₂H Me Cl OCHFCF₃ HCl OCHFCF₃ Me Cl SCF₃ H Cl SCF₃ Me Cl SCHF₂ H Cl SCHF₂ Me Cl SCH₂CF₃ HCl SCH₂CF₃ Me Cl SCF₂CF₃ H Cl SCF₂CF₃ Me Cl SCF₂CF₂H H Cl SCF₂CF₂H Me ClSCHFCF₃ H Cl SCHFCF₃ Me Cl SOCF₃ H Cl SOCF₃ Me Cl SOCHF₂ H Cl SOCHF₂ MeCl SOCH₂CF₃ H Cl SOCH₂CF₃ Me Cl SOCF₂CF₃ H Cl SOCF₂CF₃ Me Cl SOCF₂CF₂H HCl SOCF₂CF₂H Me Cl SOCHFCF₃ H Cl SOCHFCF₃ Me Cl SO₂CF₃ H Cl SO₂CF₃ Me ClSO₂CHF₂ H Cl SO₂CHF₂ Me Cl SO₂CH₂CF₃ H Cl SO₂CH₂CF₃ Me Cl SO₂CF₂CF₃ H ClSO₂CF₂CF₃ Me Cl SO₂CF₂CF₂H H Cl SO₂CF₂CF₂H Me Cl SO₂CHFCF₃ H ClSO₂CHFCF₃ Me Cl CN H Cl CN Me Br Cl H Br Cl Me Br Br H Br Br Me Br OCF₃H Br OCF₃ Me Br OCHF₂ H Br OCHF₂ Me Br OCH₂CF₃ H Br OCH₂CF₃ Me BrOCF₂CF₃ H Br OCF₂CF₃ Me Br OCF₂CF₂H H Br OCF₂CF₂H Me Br OCHFCF₃ H BrOCHFCF₃ Me Br SCF₃ H Br SCF₃ Me Br SCHF₂ H Br SCHF₂ Me Br SCH₂CF₃ H BrSCH₂CF₃ Me Br SCF₂CF₃ H Br SCF₂CF₃ Me Br SCF₂CF₂H H Br SCF₂CF₂H Me BrSCHFCF₃ H Br SCHFCF₃ Me Br SOCF₃ H Br SOCF₃ Me Br SOCHF₂ H Br SOCHF₂ MeBr SOCH₂CF₃ H Br SOCH₂CF₃ Me Br SOCF₂CF₃ H Br SOCF₂CF₃ Me Br SOCF₂CF₂H HBr SOCF₂CF₂H Me Br SOCHFCF₃ H Br SOCHFCF₃ Me Br SO₂CF₃ H Br SO₂CF₃ Me BrSO₂CHF₂ H Br SO₂CHF₂ Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃ Me Br SO₂CF₂CF₃ H BrSO₂CF₂CF₃ Me Br SO₂CF₂CF₂H H Br SO₂CF₂CF₂H Me Br SO₂CHFCF₃ H BrSO₂CHFCF₃ Me Br CN H Br CN Me

[0134] TABLE 5

T and V are both Cl and U is H Q R M Q R M Cl Cl H Cl Cl Me Cl Br H ClBr Me Cl OCF₃ H Cl OCF₃ Me Cl OCHF₂ H Cl OCHF₂ Me Cl OCH₂CF₃ H ClOCH₂CF₃ Me Cl OCF₂CF₃ H Cl OCF₂CF₃ Me Cl OCF₂CF₂ H Cl OCF₂CF₂H Me ClOCHFCF₃ H Cl OCHFCF₃ Me Cl SCF₃ H Cl SCF₃ Me Cl SCHF₂ H Cl SCHF₂ Me ClSCH₂CF₃ H Cl SCH₂CF₃ Me Cl SCF₂CF₃ H Cl SCF₂CF₃ Me Cl SCF₂CF₂ H ClSCF₂CF₂H Me Cl SCHFCF₃ H Cl SCHFCF₃ Me Cl SOCF₃ H Cl SOCF₃ Me Cl SOCHF₂H Cl SOCHF₂ Me Cl SOCH₂CF₃ H Cl SOCH₂CF₃ Me Cl SOCF₂CF₃ H Cl SOCF₂CF₃ MeCl SOCF₂CF₂H H Cl SOCF₂CF₂H Me Cl SOCHFCF₃ H Cl SOCHFCF₃ Me Cl SO₂CF₃ HCl SO₂CF₃ Me Cl SO₂CHF₂ H Cl SO₂CHF₂ Me Cl SO₂CH₂CF₃ H Cl SO₂CH₂CF₃ MeCl SO₂CF₂CF₃ H Cl SO₂CF₂CF₃ Me Cl SO₂CF₂CF₂H H Cl SO₂CF₂CF₂H Me ClSO₂CHFCF₃ H Cl SO₂CHFCF₃ Me Cl CN H Cl CN Me Br Cl H Br Cl Me Br Br H BrBr Me Br OCF₃ H Br OCF₃ Me Br OCHF₂ H Br OCHF₂ Me Br OCH₂CF₃ H BrOCH₂CF₃ Me Br OCF₂CF₃ H Br OCF₂CF₃ Me Br OCF₂CF₂H H Br OCF₂CF₂H Me BrOCHFCF₃ H Br OCHFCF₃ Me Br SCF₃ H Br SCF₃ Me Br SCHF₂ H Br SCHF₂ Me BrSCH₂CF₃ H Br SCH₂CF₃ Me Br SCF₂CF₃ H Br SCF₂CF₃ Me Br SCF₂CF₂H H BrSCF₂CF₂H Me Br SCHCF₃ H Br SCHFCF₃ Me Br SOCF₃ H Br SOCF₃ Me Br SOCHF₂ HBr SOCHF₂ Me Br SOCH₂CF₃ H Br SOCH₂CF₃ Me Br SOCF₂CF₃ H Br SOCF₂CF₃ MeBr SOCF₂CF₂H H Br SOCF₂CF₂H Me Br SOCHFCF₃ H Br SOCHFCF₃ Me Br SO₂CF₃ HBr SO₂CF₃ Me Br SO₂CHF₂ H Br SO₂CHF₂ Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃ MeBr SO₂CF₂CF₃ H Br SO₂CF₂CF₃ Me Br SO₂CF₂CF₂H H Br SO₂CF₂CF₂H Me BrSO₂CHFCF₃ H Br SO₂CHFCF₃ Me Br CN H Br CN Me T and V are both Cl and Uis Me Q R S Q R S Cl Cl H Cl Cl Me Cl Br H Cl Br Me Cl OCF₃ H Cl OCF₃ MeCl OCHF₂ H Cl OCHF₃ Me Cl OCH₂CF₃ H Cl OCH₂CF₃ Me Cl OCF₂CF₃ H ClOCF₂CF₃ Me Cl OCF₂CF₂H H Cl OCF₂CF₂H Me Cl OCHFCF₃ H Cl OCHFCF₃ Me ClSCF₃ H Cl SCF₃ Me Cl SCHF₂ H Cl SCHF₂ Me Cl SCH₂CF₃ H Cl SCH₂CF₃ Me ClSCF₂CF₃ H Cl SCF₂CF₃ Me Cl SCF₂CF₂H H Cl SCF₂CF₂H Me Cl SCHFCF₃ H ClSCHFCF₃ Me Cl SOCF₃ H Cl SOCF₃ Me Cl SOCHF₂ H Cl SOCHF₂ Me Cl SOCH₂CF₃ HCl SOCH₂CF₃ Me Cl SOCF₂CF₃ H Cl SOCF₂CF₃ Me Cl SOCF₂CF₂H H Cl SOCF₂CF₂HMe Cl SOCHFCF₃ H Cl SOCHFCF₃ Me Cl SO₂CF₃ H Cl SO₂CF₃ Me Cl SO₂CHF₂ H ClSO₂CHF₂ Me Cl SO₂CH₂CF₃ H Cl SO₂CH₂CF₃ Me Cl SO₂CF₂CF₃ H Cl SO₂CF₂CF₃ MeCl SO₂CF₂CF₂H H Cl SO₂CF₂CF₂H Me Cl SO₂CHFCF₃ H Cl SO₂CHFCF₃ Me Cl CN HCl CN Me Br Cl H Br Cl Me Br Br H Br Br Me Br OCF₃ H Br OCF₃ Me Br OCHF₂H Br OCHF₂ Me Br OCH₂CF₃ H Br OCH₂CF₃ Me Br OCF₂CF₃ H Br OCF₂CF₃ Me BrOCF₂CF₂H Cl Br OCF₂CF₂H Me Br OCHFCF₃ H Br OCHFCF₃ Me Br SCF₃ H Br SCF₃Me Br SCHF₂ H Br SCHF₂ Me Br SCH₂CF₃ H Br SCH₂CF₃ Me Br SCF₂CF₃ H BrSCF₂CF₃ Me Br SCF₂CF₂H H Br SCF₂CF₂H Me Br SCHFCF₃ H Br SCHFCF₃ Me BrSOCF₃ H Br SOCF₃ Me Br SOCHF₂ H Br SOCHF₂ Me Br SOCH₂CF₃ H Br SOCH₂CF₃Me Br SOCF₂CF₃ H Br SOCF₂CF₃ Me Br SOCF₂CF₂H H Br SOCF₂CF₂H Me BrSOCHFCF₃ H Br SOCHFCF₃ Me Br SO₂CF₃ H Br SO₂CF₃ Me Br SO₂CHF₂ H BrSO₂CHF₂ Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃ Me Br SO₂CF₂CF₃ H Br SO₂CF₂CF₃ MeBr SO₂CF₂CF₂H H Br SO₂CF₂CF₂H Me Br SO₂CHFCF₃ H Br SO₂CHFCF₃ Me Br CN HBr CN Me T is Cl and V and U are both Me Cl Cl H Cl Cl Me Cl Br H Cl BrMe Cl OCF₃ H Cl OCF₃ Me Cl OCHF₂ H Cl OCHF₃ Me Cl OCH₂CF₃ H Cl OCH₂CF₃Me Cl OCF₂CF₃ H Cl OCF₂CF₃ Me Cl OCF₂CF₂H H Cl OCF₂CF₂H Me Cl OCHFCF₃ HCl OCHFCF₃ Me Cl SCF₃ H Cl SCF₃ Me Cl SCHF₂ H Cl SCHF₂ Me Cl SCH₂CF₃ HCl SCH₂CF₃ Me Cl SCF₂CF₃ H Cl SCF₂CF₃ Me Cl SCF₂CF₂H H Cl SCF₂CF₂H Me ClSCHFCF₃ H Cl SCHFCF₃ Me Cl SOCF₃ H Cl SOCF₃ Me Cl SOCHF₂ H Cl SOCHF₂ MeCl SOCH₂CF₃ H Cl SOCH₂CF₃ Me Cl SOCF₂CF₃ H Cl SOCF₂CF₃ Me Cl SOCF₂CF₂H HCl SOCF₂CF₂H Me Cl SOCHFCF₃ H Cl SOCHFCF₃ Me Cl SO₂CF₃ H Cl SO₂CF₃ Me ClSO₂CHF₂ H Cl SO₂CHF₂ Me Cl SO₂CH₂CF₃ H Cl SO₂CH₂CF₃ Me Cl SO₂CF₂CF₃ H ClSO₂CF₂CF₃ Me Cl SO₂CF₂CF₂H H Cl SO₂CF₂CF₂H Me Cl SO₂CHFCF₃ H ClSO₂CHFCF₃ Me Cl CN H Cl CN Me Br Cl H Br Cl Me Br Br H Br Br Me Br OCF₃H Br OCF₃ Me Br OCHF₂ H Br OCHF₂ Me Br OCH₂CF₃ H Br OCH₂CF₃ Me BrOCF₂CF₃ H Br OCF₂CF₃ Me Br OCF₂CF₂H H Br OCF₂CF₂H Me Br OCHFCF₃ H BrOCHFCF₃ Me Br SCF₃ H Br SCF₃ Me Br SCHF₂ H Br SCHF₂ Me Br SCH₂CF₃ H BrSCH₂CF₃ Me Br SCF₂CF₃ H Br SCF₂CF₃ Me Br SCF₂CF₂H H Br SCF₂CF₂H Me BrSCHFCF₃ H Br SCHFCF₃ Me Br SOCF₃ H Br SOCF₃ Me Br SOCHF₂ H Br SOCHF₂ MeBr SOCH₂CF₃ H Br SOCH₂CF₃ Me Br SOCF₂CF₃ H Br SOCF₂CF₃ Me Br SOCF₂CF₂H HBr SOCF₂CF₂H Me Br SOCHFCF₃ H Br SOCHFCF₃ Me Br SO₂CF₃ H Br SO₂CF₃ Me BrSO₂CHF₂ H Br SO₂CHF₂ Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃ Me Br SO₂CF₂CF₃ H BrSO₂CF₂CF₃ Me Br SO₂CF₂CF₂H H Br SO₂CF₂CF₂H Me Br SO₂CHFCF₃ H BrSO₂CHFCF₃ Me Br CN H Br CN Me

[0135] TABLE 6

T and V are both Cl and U is H Q R M Q R M Cl Cl H Cl Cl Me Cl Br H ClBr Me Cl CF₃ H Cl CF₃ Me Cl OCF₃ H Cl OCF₃ Me Cl OCHF₂ H Cl OCHF₂ Me ClOCH₂CF₃ H Cl OCH₂CF₃ Me Cl OCF₂CF₃ H Cl OCF₂CF₃ Me Cl OCF₂CF₂H H ClOCF₂CF₂H Me Cl OCHFCF₃ H Cl OCHFCF₃ Me Cl SCF₃ H Cl SCF₃ Me Cl SCHF₂ HCl SCHF₂ Me Cl SCH₂CF₃ H Cl SCH₂CF₃ Me Cl SCF₂CF₃ H Cl SCF₂CF₃ Me ClSCF₂CF₂H H Cl SCF₂CF₂H Me Cl SCHFCF₃ H Cl SCHFCF₃ Me Cl SOCF₃ H Cl SOCF₃Me Cl SOCHF₂ H Cl SOCHF₂ Me Cl SOCH₂CF₃ H Cl SOCH₂CF₃ Me Cl SOCF₂CF₃ HCl SOCF₂CF₃ Me Cl SOCF₂CF₂H H Cl SOCF₂CF₂H Me Cl SOCHFCF₃ H Cl SOCHFCF₃Me Cl SO₂CF₃ H Cl SO₂CF₃ Me Cl SO₂CHF₂ H Cl SO₂CHF₂ Me Cl SO₂CH₂CF₃ H ClSO₂CH₂CF₃Me Cl SO₂CF₂CF₃ H Cl SO₂CF₂CF₃Me Cl SO₂CF₂CF₂H H Cl SO₂CF₂CF₂HMe Cl SO₂CHFCF₃ H Cl SO₂CHFCF₃Me Cl CN H Cl CN Me Cl H Cl Cl Me Cl Cl HBr Cl Me Br Cl H CF₃ Cl Me CF₃ Cl H OCF₃ Cl Me OCF₃ Cl H OCHF₂ Cl MeOCHF₂ Cl H OCH₂CF₃ Cl Me OCH₂CF₃ Cl H OCF₂CF₂H Cl Me OCF₂CF₂H Cl H SCF₃Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ Br Cl H Br Cl Me Br Br H Br Br Me BrCF₃ H Br CF₃ Me Br OCF₃ H Br OCF₃ Me Br OCHF₂ H Br OCHF₂ Me Br OCH₂CF₃ HBr OCH₂CF₃ Me Br OCF₂CF₃ H Br OCF₂CF₃ Me Br OCF₂CF₂H H Br OCF₂CF₂H Me BrOCHFCF₃ H Br OCHFCF₃ Me Br SCF₃ H Br SCF₃ Me Br SCHF₂ H Br SCHF₂ Me BrSCH₂CF₃ H Br SCH₂CF₃ Me Br SCF₂CF₃ H Br SCF₂CF₃ Me Br SCF₂CF₂H H BrSCF₂CF₂H Me Br SCHFCF₃ H Br SCHFCF₃ Me Br SOCF₃ H Br SOCF₃ Me Br SOCHF₂H Br SOCHF₂ Me Br SOCH₂CF₃ H Br SOCH₂CF₃ Me Br SOCF₂CF₃ H Br SOCF₂CF₃ MeBr SOCF₂CF₂H H Br SOCF₂CF₂H Me Br SOCHFCF₃ H Br SOCHFCF₃Me Br SO₂CF₃ HBr SO₂CF₃ Me Br SO₂CHF₂ H Br SO₂CHF₂ Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃ MeBr SO₂CF₂CF₃ H Br SO₂CF₂CF₃ Me Br SO9 CF₂CF₂H H Br SO₂CF₂CF₂H Me BrSO₂CHFCF₃ H Br SO₂CHFCF₃ Me Br CN H Br CN Me H Cl Cl Me Cl Cl H Br Cl MeBr Cl H CF₃ Cl Me CF₃ Cl H OCF₃ Cl Me OCF₃ Cl H OCHF₂ Cl Me OCHF₂ Cl HOCH₂CF₃ Cl Me OCH₂CF₃ Cl H OCF₂CF₃ Cl Me OCF₂CF₃ Cl H OCF₂CF₂H Cl MeOCF₂CF₂H Cl H OCHFCF₃ Cl Me OCHFCF₃ Cl H SCF₃ Cl Me SCF₃ Cl H SCHF₂ ClMe SCHF₂ Cl H SCH₂CF₃ Cl Me SCH₂CF₃ Cl H SCF₂CF₃ Cl Me SCF₂CF₃ Cl HSCF₂CF₂H Cl Me SCF₂CF₂H Cl H SCHFCF₃ Cl Me SCHFCF₃ Cl H SOCF₃ Cl MeSOCF₃ Cl H SOCHF₂ Cl Me SOCHF₂ Cl H SOCH₂CF₃ Cl Me SOCH₂CF₃Cl H SOCF₂CF₃Cl Me SOCF₂CF₃Cl H SOCF₂CF₂H Cl Me SOCF₂CF₂H Cl H SOCHFCF₃ Cl MeSOCHFCF₃ Cl H SO₂CF₃ Cl Me SO₂CF₃ Cl H SO₂CHF₂ Cl Me SO₂CHF₂ Cl HSO₂CH₂CF₃ Cl Me SO₂CH₂CF₃ Cl H SO₂CF₂CF₃ Cl Me SO₂CF₂CF₃ Cl H SO₂CF₂CF₂HCl Me SO₂CF₂CF₂H Cl H SO₂CHFCF₃ Cl Me SO₂CHFCF₃ Cl H CN Cl Me CN Cl ClCl H Cl Cl Me Cl Br H Cl Br Me Cl CF₃ H Cl CF₃ Me Cl OCF₃ H Cl OCF₃ MeCl OCHF₂ H Cl OCHF₂ Me Cl OCH₂CF₃ H Cl OCH₂CF₃ Me Cl OCF₂CF₃ H ClOCF₂CF₃ Me Cl OCF₂CF₂H H Cl OCF₂CF₂H Me Cl OCFCF₃ H Cl OCHFCF₃ Me ClSCF₃ H Cl SCF₃ Me Cl SCHF₂ H Cl SCHF₂ Me Cl SCH₂CF₃ H Cl SCH₂CF₃ Me ClSCF₂CF₃ H Cl SCF₂CF₃ Me Cl SCF₂CF₂H H Cl SCF₂CF₂H Me Cl SCHFCF₃ H ClSCHFCF₃ Me Cl SOCF₃ H Cl SOCF₃ Me Cl SOCHF₂ H Cl SOCHF₂ Me Cl SOCH₂CF₃ HCl SOCH₂CF₃Me Cl SOCF₂CF₃ H Cl SOCF₂CF₃Me Cl SOCF₂CF₂H H Cl SOCF₂CF₂H MeCl SOCHFCF₃ H Cl SOCHFCF₃ Me Cl SO₂CF₃ H Cl SO₂CF₃ Me Cl SO₂CHF₂ H ClSO₂CHF₂ Me Cl SO₂CH₂CF₃ H Cl SO₂CH₂CF₃ Me Cl SO₂CF₂CF₃ H Cl SO₂CF₂CF₃ MeCl SO₂CF₂CF₂H H Cl SO₂CF₂CF₂H Me Cl SO₂CHFCF₃ H Cl SO₂CHFCF₃ Me Cl CN HCl CN Me Cl H Cl Cl Me Cl Cl H Br Cl Me Br Cl H CF₃ Cl Me CF₃ Cl H OCF₃Cl Me OCF₃ Cl H OCHF₂ Cl Me OCHF₂ Cl H OCH₂CF₃ Cl Me OCH₂CF₃ Cl HOCF₂CF₂H Cl Me OCF₂CF₂H Cl H SCF₃ Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ BrSCF₃ H Br SCF₃ Me Br SCHF₂ H Br SCHF₂ Me Br SCH₂CF₃ H Br SCH₂CF₃ Me BrSCF₂CF₃ H Br SCF₂CF₃ Me Br SCF₂CF₂H H Br SCF₂CF₂H Me Br SCHFCF₃ H BrSCHFCF₃ Me Br SOCF₃ H Br SOCF₃ Me Br SOCHF₂ H Br SOCHF₂ Me Br SOCH₂CF₃ HBr SOCH₂CF₃ Me Br SOCF₂CF₃ H Br SOCF₂CF₃ Me Br SOCF₂CF₂H H Br SOCF₂CF₂HMe Br SOCHFCF₃ H Br SOCHFCF₃ Me Br SO₂CF₃ H Br SO₂CF₃ Me Br SO₂CHF₂ H BrSO₂CHF₂ Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃ Me Br SO₂CF₂CF₃ H Br SO₂CF₂CF₃MeBr SO₂CF₂CF₂H H Br SO₂CF₂CF₂H Me Br SO₂CHFCF₃ H Br SO₂CHFCF₃ Me Br CN HBr CN Me H Cl Cl Me Cl Cl H Br Cl Me Br Cl H CF₃ Cl Me CF₃ Cl H OCF₃ ClMe OCF₃ Cl H OCHF₂ Cl Me OCHF₂ Cl H OCH₂CF₃ Cl Me OCH₂CF₃ Cl H OCF₂CF₃Cl Me OCF₂CF₃ Cl H OCF₂CF₂H Cl Me OCF₂CF₂H Cl H OCHFCF₃ Cl Me OCHFCF₃ ClH SCF₃ Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ Cl H SCH₂CF₃ Cl Me SCH₂CF₃ Cl HSCF₂CF₃ Cl Me SCF₂CF₃ Cl H SCF₂CF₂H Cl Me SCF₂CF₂H Cl H SCHFCF₃ Cl MeSCHFCF₃ Cl H SOCF₃ Cl Me SOCF₃ Cl H SOCHF₂ Cl Me SOCHF₂ Cl H SOCH₂CF₃ ClMe SOCH₂CF₃Cl H SOCF₂CF₃ Cl Me SOCF₂CF₃Cl H SOCF₂CF₂H Cl Me SOCF₂CF₂H ClH SOCHFCF₃ Cl Me SOCHFCF₃Cl H SO₂CF₃ Cl Me SO₂CF₃ Cl H SO₂CHF₂ Cl MeSO₂CHF₂ Cl H SO₂CH₂CF₃ Cl Me SO₂CH₂CF₃ Cl H SO₂CF₂CF₃ Cl Me SO₂CF₂CF₃ ClH SO₂CF₂CF₂H Cl Me SO₂CF₂CF₂H Cl H SO₂CHFCF₃ Cl Me SO₂CHFCF₃Cl H CN ClMe CN Cl T is Cl and V and U are both Me Q R S Q R S Cl Cl H Cl Cl Me ClBr H Cl Br Me Cl CF₃ H Cl CF₃ Me Cl OCF₃ H Cl OCF₃ Me Cl OCHF₂ H ClOCHF₂ Me Cl OCH₂CF₃ H Cl OCH₂CF₃ Me Cl OCF₂CF₃ H Cl OCF₂CF₃ Me ClOCF₂CF₂H H Cl OCF₂CF₂H Me Cl OCHFCF₃ H Cl OCHFCF₃ Me Cl SCF₃ H Cl SCF₃Me Cl SCHF₂ H Cl SCHF₂ Me Cl SCH₂CF₃ H Cl SCH₂CF₃ Me Cl SCF₂CF₃ H ClSCF₂CF₃ Me Cl SCF₂CF₂H H Cl SCF₂CF₂H Me Cl SCHFCF₃ H Cl SCHFCF₃ Me ClSOCF₃ H Cl SOCF₃ Me Cl SOCHF₂ H Cl SOCHF₂ Me Cl SOCH₂CF₃ H Cl SOCH₂CF₃Me Cl SOCF₂CF₃ H Cl SOCF₂CF₃ Me Cl SOCF₂CF₂H H Cl SOCF₂CF₂H Me ClSOCHFCF₃ H Cl SOCHFCF₃ Me Cl SO₂CF₃ H Cl SO₂CF₃ Me Cl SO₂CHF₂ H ClSO₂CHF₂ Me Cl SO₂CH₂CF₃ H Cl SO₂CH₂CF₃ Me Cl SO₂CF₂CF₃ H Cl SO₂CF₂CF₃ MeCl SO₂CF₂CF₂H H Cl SO₂CF₂CF₂H Me Cl SO₂CHFCF₃ H Cl SO₂CHFCF₃ Me Cl CN HCl CN Me Cl H Cl Cl Me Cl Cl H Br Cl Me Br Cl H CF₃ Cl Me CF₃ Cl H OCF₃Cl Me OCF₃ Cl H OCHF₂ Cl Me OCHF₂ Cl H OCH₂CF₃ Cl Me OCH₂CF₃ Cl HOCF₂CF₂H Cl Me OCF₂CF₂H Cl H SCF₃ Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ BrSCF₃ H Br SCF₃ Me Br SCHF₂ H Br SCHF₂ Me Br SCH₂CF₃ H Br SCH₂CF₃ Me BrSCF₂CF₃ H Br SCF₂CF₃ Me Br SCF₂CF₂H H Br SCF₂CF₂H Me Br SCHFCF₃ H BrSCHFCF₃ Me Br SOCF₃ H Br SOCF₃ Me Br SOCHF₂ H Br SOCHF₂ Me Br SOCH₂CF₃ HBr SOCH₂CF₃ Me Br SOCF₂CF₃ H Br SOCF₂CF₃ Me Br SOCF₂CF₂H H Br SOCF₂CF₂HMe Br SOCHFCF₃ H Br SOCHFCF₃ Me Br SO₂CF₃ H Br SO₂CF₃ Me Br SO₂CHF₂ H BrSO₂CHF₂ Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃Me Br SO₂CF₂CF₃ H Br SO₂CF₂CF₃MeBr SO₂CF₂CF₂H H Br SO₂CF₂CF₂H Me Br SO₂CHFCF₃ H Br SO₂CHFCF₃Me Br CN HBr CN Me H Cl Cl Me Cl Cl H Br Cl Me Br Cl H CF₃ Cl Me CF₃ Cl H OCF₃ ClMe OCF₃ Cl H OCHF₂ Cl Me OCHF₂ Cl H OCH₂CF₃ Cl Me OCH₂CF₃ Cl H OCF₂CF₃Cl Me OCF₂CF₃ Cl H OCF₂CF₂H Cl Me OCF₂CF₂H Cl H OCHFCF₃ Cl Me OCHFCF₃ ClH SCF₃ Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ Cl H SCH₂CF₃ Cl Me SCH₂CF₃ Cl HSCF₂CF₃ Cl Me SCF₂CF₃ Cl H SCF₂CF₂H Cl Me SCF₂CF₂H Cl H SCHFCF₃ Cl MeSCHFCF₃ Cl H SOCF₃ Cl Me SOCF₃ Cl H SOCHF₂ Cl Me SOCHF₂ Cl H SOCH₂CF₃ ClMe SOCH₂CF₃ Cl H SOCF₂CF₃ Cl Me SOCF₂CF₃ Cl H SOCF₂CF₂H Cl Me SOCF₂CF₂HCl H SOCHFCF₃ Cl Me SOCHFCF₃Cl H SO₂CF₃ Cl Me SO₂CF₃ Cl H SO₂CHF₂ Cl MeSO₂CHF₂ Cl H SO₂CH₂CF₃ Cl Me SO₂CH₂CF₃ Cl H SO₂CF₂CF₃ Cl Me SO₂CF₂CF₃ ClH SO₂CF₂CF₂H Cl Me SO₂CF₂CF₂H Cl H SO₂CHFCF₃ Cl Me SO₂CHFCF₃ Cl H CN ClMe CN Cl

[0136] TABLE 7

T and V are both Cl and U is H Q R M Q R M Cl Cl H Cl Cl Me Cl Br H ClBr Me Cl CF₃ H Cl CF₃ Me Cl OCF₃ H Cl OCF₃ Me Cl OCHF₂ H Cl OCHF₂ Me ClOCH₂CF₃ H Cl OCH₂CF₃ Me Cl OCF₂CF₃ H Cl OCF₂CF₃ Me Cl OCF₂CF₂H H ClOCF₂CF₂H Me Cl OCHFCF₃ H Cl OCHFCF₃ Me Cl SCF₃ H Cl SCF₃ Me Cl SCHF₂ HCl SCHF₂ Me Cl SCH₂CF₃ H Cl SCH₂CF₃ Me Cl SCF₂CF₃ H Cl SCF₂CF₃ Me ClSCF₂CF₂H H Cl SCF₂CF₂H Me Cl SCHFCF₃ H Cl SCHFCF₃ Me Cl SOCF₃ H Cl SOCF₃Me Cl SOCHF₂ H Cl SOCHF₂ Me Cl SOCH₂CF₃ H Cl SOCH₂CF₃ Me Cl SOCF₂CF₃ HCl SOCF₂CF₃ Me Cl SOCF₂CF₂H H Cl SOCF₂CF₂H Me Cl SOCHFCF₃ H Cl SOCHFCF₃Me Cl SO₂CF₃ H Cl SO₂CF₃ Me Cl SO₂CHF₂ H Cl SO₂CHF₂ Me Cl SO₂CH₂CF₃ H ClSO₂CH₂CF₃ Me Cl SO₂CF₂CF₃ H Cl SO₂CF₂CF₃ Me Cl SO₂CF₂CF₂H H ClSO₂CF₂CF₂H Me Cl SO₂CHFCF₃ H Cl SO₂CHFCF₃Me Cl CN H Cl CN Me Cl H Cl ClMe Cl Cl H Br Cl Me Br Cl H CF₃ Cl Me CF₃ Cl H OCF₃ Cl Me OCF₃ Cl HOCHF₂ Cl Me OCHF₂ Cl H OCH₂CF₃ Cl Me OCH₂CF₃ Cl H OCF₂CF₂H Cl MeOCF₂CF₂H Cl H SCF₃ Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ Br Cl H Br Cl Me BrBr H Br Br Me Br CF₃ H Br CF₃ Me Br OCF₃ H Br OCF₃ Me Br OCHF₂ H BrOCHF₂ Me Br OCH₂CF₃ H Br OCH₂CF₃ Me Br OCF₂CF₃ H Br OCF₂CF₃ Me BrOCF₂CF₂H H Br OCF₂CF₂H Me Br OCHFCF₃ H Br OCHFCF₃ Me Br SCF₃ H Br SCF₃Me Br SCHF₂ H Br SCHF₂ Me Br SCH₂CF₃ H Br SCH₂CF₃ Me Br SCF₂CF₃ H BrSCF₂CF₃ Me Br SCF₂CF₂H H Br SCF₂CF₂H Me Br SCHFCF₃ H Br SCHFCF₃ Me BrSOCF₃ H Br SOCF₃ Me Br SOCHF₂ H Br SOCHF₂ Me Br SOCH₂CF₃ H Br SOCH₂CF₃Me Br SOCF₂CF₃ H Br SOCF₂CF₃ Me Br SOCF₂CF₂H H Br SOCF₂CF₂H Me BrSOCHFCF₃ H Br SOCHFCF₃Me Br SO₂CF₃ H Br SO₂CF₃ Me Br SO₂CHF₂ H BrSO₂CHF, Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃Me Br SO₂CF₂CF₃ H Br SO₂CF₂CF₃MeBr SO₂CF₂CF₂H H Br SO₂CF₂CF₂H Me Br SO₂CHIFCF₃ H Br SO₂CHFCF₃Me Br CN HBr CN Me H Cl Cl Me Cl Cl H Br Cl Me Br Cl H CF₃ Cl Me CF₃ Cl H OCF₃ ClMe OCF₃ Cl H OCHF₂ Cl Me OCHF₂ Cl H OCH₂CF₃ Cl Me OCH₂CF₃ Cl H OCF₂CF₃Cl Me OCF₂CF₃ Cl H OCF₂CF₂H Cl Me OCF₂CF₂H Cl H OCHFCF₃ Cl Me OCHFCF₃ ClH SCF₃ Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ Cl H SCH₂CF₃ Cl Me SCH₂CF₃ Cl HSCF₂CF₃ Cl Me SCF₂CF₃ Cl H SCF₂CF₂H Cl Me SCF₂CF₂H Cl H SCHFCF₃ Cl MeSCHFCF₃ Cl H SOCF₃ Cl Me SOCF₃ Cl H SOCHF₂ Cl Me SOCHF₂ Cl H SOCH₂CF₃ ClMe SOCH₂CF₃ Cl H SOCF₂CF₃ Cl Me SOCF₂CF₃ Cl H SOCF₂CF₂H Cl Me SOCF₂CF₂HCl H SOCHFCF₃ Cl Me SOCHFCF₃ Cl H SO₂CF₃ Cl Me SO₂CF₃ Cl H SO₂CHF₂ Cl MeSO₂CHF₂ Cl H SO₂CH₂CF₃ Cl Me SO₂CH₂CF₃ Cl H SO₂CF₂CF₃ Cl Me SO₂CF₂CF₃ ClH SO₂CF₂CF₂H Cl Me SO₂CF₂CF₂H Cl H SO₂CHFCF₃ Cl Me SO₂CHFCF₃ Cl H CN ClMe CN Cl T and V are both Cl and U is Me Q R S Q R S Cl Cl H Cl Cl Me ClBr H Cl Br Me Cl CF₃ H Cl CF₃ Me Cl OCF₃ H Cl OCF₃ Me Cl OCHF₂ H ClOCIHF₂ Me Cl OCH₂CF₃ H Cl OCH₂CF₃ Me Cl OCF₂CF₃ H Cl OCF₂CF₃ Me ClOCF₂CF₂H H Cl OCF₂CF₂H Me Cl OCHFCF₃ H Cl OCHFCF₃ Me Cl SCF₃ H Cl SCF₃Me Cl SCHF₂ H Cl SCHF₂ Me Cl SCH₂CF₃ H Cl SCH₂CF₃ Me Cl SCF₂CF₃ H ClSCF₂CF₃ Me Cl SCF₂CF₂H H Cl SCF₂CF₂H Me Cl SCHFCF₃ H Cl SCHFCF₃ Me ClSOCF₃ H Cl SOCF₃ Me Cl SOCHF₂ H Cl SOCHF₂ Me Cl SOCH₂CF₃ H Cl SOCH₂CF₃MeCl SOCF₂CF₃ H Cl SOCF₂CF₃Me Cl SOCF₂CF₂H H Cl SOCF₂CF₂H Me Cl SOCHFCF₃ HCl SOCHFCF₃ Me Cl SO₂CF₃ H Cl SO₂CF₃ Me Cl SO₂CHF₂ H Cl SO₂CHF₂ Me ClSO₂CH₂CF₃ H CL SO₂CH9CF₃Me Cl SO₂CF₂CF₃ H Cl SO₂CF₂CF₃Me Cl SO₂CF₂CF₂H HCl SO₂CF₂CF₂H Me Cl SO₂CHFCF₃ H Cl SO₂CHFCF₃ Me Cl CN H Cl CN Me Cl H ClCl Me Cl Cl H Br Cl Me Br Cl H CF₃ Cl Me CF₃ Cl H OCF₃ Cl Me OCF₃ Cl HOCHF₂ Cl Me OCHF₂ Cl H OCH₂CF₃ Cl Me OCH₂CF₃ Cl H OCF₂CF₂H Cl MeOCF₂CF₂H Cl H SCF₃ Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ Br SCF₃ H Br SCF₃Me Br SCHF₂ H Br SCHF₂ Me Br SCH₂CF₃ H Br SCH₂CF₃ Me Br SCF₂CF₃ H BrSCF₂CF₃ Me Br SCF₂CF₂H H Br SCF₂CF₂H Me Br SCHFCF₃ H Br SCHFCF₃ Me BrSOCF₃ H Br SOCF₃ Me Br SOCHF₂ H Br SOCHF₂ Me Br SOCH₂CF₃ H Br SOCH₂CF₃Me Br SOCF₂CF₃ H Br SOCF₂CF₃ Me Br SOCF₂CF₂H H Br SOCF₂CF₂H Me BrSOCHFCF₃ H Br SOCHFCF₃ Me Br SO₂CF₃ H Br SO₂CF₃ Me Br SO₂CHF₂ H BrSO₂CHF₂ Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃ Me Br SO₂CF₂CF₃ H Br SO₂CF₂CF₃MeBr SO₂CF₂CF₂H H Br SO₂CF₂CF₂H Me Br SO₂CHFCF₃ H Br SO₂CHFCF₃ Me Br CN HBr CN Me H Cl Cl Me Cl Cl H Br Cl Me Br Cl H CF₃ Cl Me CF₃ Cl H OCF₃ ClMe OCF₃ Cl H OCHF₂ Cl Me OCHF₂ Cl H OCH₂CF₃ Cl Me OCH₂CF₃ Cl H OCF₂CF₃Cl Me OCF₂CF₃ Cl H OCF₂CF₂H Cl Me OCF₂CF₂H Cl H OCHFCF₃ Cl Me OCHFCF₃ ClH SCF₃ Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ Cl H SCH₂CF₃ Cl Me SCH₂CF₃ Cl HSCF₂CF₃ Cl Me SCF₂CF₃ Cl H SCF₂CF₂H Cl Me SCF₂CF₂H Cl H SCHFCF₃ Cl MeSCHFCF₃ Cl H SOCF₃ Cl Me SOCF₃ Cl H SOCHF₂ Cl Me SOCHF₂ Cl H SOCH₂CF₃ ClMe SOCH₂CF₃Cl H SOCF₂CF₃ Cl Me SOCF₂CF₃Cl H SOCF₂CF₂H Cl Me SOCF₂CF₂H ClH SOCHFCF₃ Cl Me SOCHFCF₃Cl H SO₂CF₃ Cl Me SO₂CF₃ Cl H SO₂CHF₂ Cl MeSO₂CHF₂ Cl H SO₂CH₂CF₃ Cl Me SO₂CH₂CF₃ Cl H SO₂CF₂CF₃ Cl Me SO₂CF₂CF₃ ClH SO₂CF₂CF₂H Cl Me SO₂CF₂CF₂H Cl H SO₂CHFCF₃ Cl Me SO₂CHFCF₃ Cl H CN ClMe CN Cl Cl Cl H Cl Cl Me Cl Br H Cl Br Me Cl CF₃ H Cl CF₃ Me Cl OCF₃ HCl OCF₃ Me Cl OCHF₂ H Cl OCHF₂ Me Cl OCH₂CF₃ H Cl OCH₂CF₃ Me Cl OCF₂CF₃H Cl OCF₂CF₃ Me Cl OCF₂CF₂H H Cl OCF₂CF₂H Me Cl OCHFCF₃ H Cl OCHFCF₃ MeCl SCF₃ H Cl SCF₃ Me Cl SCHF₂ H Cl SCHF₂ Me Cl SCH₂CF₃ H Cl SCH₂CF₃ MeCl SCF₂CF₃ H Cl SCF₂CF₃ Me Cl SCF₂CF₂H H Cl SCF₂CF₂H Me Cl SCHFCF₃ H ClSCHFCF₃ Me Cl SOCF₃ H Cl SOCF₃ Me Cl SOCIIF₂ H Cl SOCHF₂ Me Cl SOCH₂CF₃H Cl SOCH₂CF₃ Me Cl SOCF₂CF₃ H Cl SOCF₂CF₃ Me Cl SOCF₂CF₂H H ClSOCF₂CF₂H Me Cl SOCHFCF₃ H Cl SOCHFCF₃ Me Cl SO₂CF₃ H Cl SO₂CF₃ Me ClSO₂CHF₂ H Cl SO₂CHF₂ Me Cl SO₂CH₂CF₃ H Cl SO₂CH₂CF₃ Me Cl SO₂CF₂CF₃ H ClSO₂CF₂CF₃ Me Cl SO₂CF₂CF₂H H Cl SO₂CF₂CF₂H Me Cl SO₂CHFCF₃ H ClSO₂CHFCF₃Me Cl CN H Cl CN Me Cl H Cl Cl Me Cl Cl H Br Cl Me Br Cl H CF₃Cl Me CF₃ Cl H OCF₃ Cl Me OCF₃ Cl H OCHF₂ Cl Me OCHF₂ Cl H OCH₂CF₃ Cl MeOCH₂CF₃ Cl H OCF₂CF₂H Cl Me OCF₂CF₂H Cl H SCF₃ Cl Me SCF₃ Cl H SCHF₂ ClMe SCHF₂ Br SCF₃ H Br SCF₃ Me Br SCHF₂ H Br SCHF₂ Me Br SCH₂CF₃ H BrSCH₂CF₃ Me Br SCF₂CF₃ H Br SCF₂CF₃ Me Br SCF₂CF₂H H Br SCF₂CF₂H Me BrSCHFCF₃ H Br SCHFCF₃ Me Br SOCF₃ H Br SOCF₃ Me Br SOCHF₂ H Br SOCHF₂ MeBr SOCH₂CF₃ H Br SOCH₂CF₃ Me Br SOCF₂CF₃ H Br SOCF₂CF₃ Me Br SOCF₂CF₂H HBr SOCF₂CF₂H Me Br SOCHFCF₃ H Br SOCHFCF₃ Me Br SO₂CF₃ H Br SO₂CF₃ Me BrSO₂CHF₂ H Br SO₂CHF₂ Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃ Me Br SO₂CF₂CF₃ H BrSO₂CF₂CF₃ Me Br SO₂CF₂CF₂H H Br SO₂CF₂CF₂H Me Br SO₂CHFCF₃ H BrSO₂CHFCF₃Me Br CN H Br CN Me H Cl Cl Me Cl Cl H Br Cl Me Br Cl H CF₃ ClMe CF₃ Cl H OCF₃ Cl Me OCF₃ Cl H OCHF₂ Cl Me OCHF₂ Cl H OCH₂CF₃ Cl MeOCH₂CF₃ Cl H OCF₂CF₃ Cl Me OCF₂CF₃ Cl H OCF₂CF₂H Cl Me OCF₂CF₂H Cl HOCHFCF₃ Cl Me OCHFCF₃ Cl H SCF₃ Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ Cl HSCH₂CF₃ Cl Me SCH₂CF₃ Cl H SCF₂CF₃ Cl Me SCF₂CF₃ Cl H SCF₂CF₂H Cl MeSCF₂CF₂H Cl H SCHFCF₃ Cl Me SCHFCF₃ Cl H SOCF₃ Cl Me SOCF₃ Cl H SOCHF₂Cl Me SOCHF₂ Cl H SOCH₂CF₃ Cl Me SOCH₂CF₃ Cl H SOCF₂CF₃ Cl Me SOCF₂CF₃Cl H SOCF₂CF₂H Cl Me SOCF₂CF₂H Cl H SOCHFCF₃ Cl Me SOCHFCF₃Cl H SO₂CF₃Cl Me SO₂CF₃ Cl H SO₂CHF₂ Cl Me SO₂CHF₂ Cl H SO₂CH₂CF₃ Cl Me SO₂CH₂CF₃Cl H SO₂CF₂CF₃ Cl Me SO2CF₂CF₃ Cl H SO₂CF₂CF₂H Cl Me SO₂CF₂CF₂H Cl HSO₂CHFCF₃ Cl Me SO₂CHFCF₃ Cl H CN Cl Me CN Cl

[0137] TABLE 8

T and V are both Cl and u is H Q R M Q R M Cl Cl H Cl Cl Me Cl Br H ClBr Me Cl CF₃ H Cl CF₃ Me Cl OCF₃ H Cl OCF₃ Me Cl OCHF₂ H Cl OCHF₂ Me ClOCH₂CF₃ H Cl OCH₂CF₃ Me Cl OCF₂CF₃ H Cl OCF₂CF₃ Me Cl OCF₂CF₂H H ClOCF₂CF₂H Me Cl OCHFCF₃ H Cl OCHFCF₃ Me Cl SCF₃ H Cl SCF₃ Me Cl SCHF₂ HCl SCHF₂ Me Cl SCH₂CF₃ H Cl SCH₂CF₃ Me Cl SCF₂CF₃ H Cl SCF₂CF₃ Me ClSCF₂CF₂H H Cl SCF₂CF₂H Me Cl SCHFCF₃ H Cl SCHFCF₃ Me Cl SOCF₃ H Cl SOCF₃Me Cl SOCHF₂ H Cl SOCHF₂ Me Cl SOCH₂CF₃ H Cl SOCH₂CF₃ Me Cl SOCF₂CF₃ HCl SOCF₂CF₃ Me Cl SOCF₂CF₂H H Cl SOCF₂CF₂H Me Cl SOCHFCF₃ H Cl SOCHFCF₃Me Cl SO₂CF₃ H Cl SO₂CF₃ Me Cl SO₂CHF₂ H Cl SO₂CHF₂ Me Cl SO₂CH₂CF₃ H ClSO₂CH₂CF₃Me Cl SO₂CF₂CF₃ H Cl SO₂CF₂CF₃Me Cl SO₂CF₂CF₂H H Cl SO₂CF₂CF₂HMe Cl SO₂CHFCF₃ H Cl SO₂CHFCF₃ Me Cl CN H Cl CN Me Cl H Cl Cl Me Cl Cl HBr Cl Me Br Cl H CF3 Cl Me CF3 Cl H OCF3 Cl Me OCF3 Cl H OCHF2 Cl MeOCHF2 Cl H OCH2CF3 Cl Me OCH2CF3 Cl H OCF2CF2H Cl Me OCF2CF2H Cl H SCF3Cl Me SCF3 Cl H SCHF2 Cl Me SCHF2 Br Cl H Br Cl Me Br Br H Br Br Me BrCF₃ H Br CF₃ Me Br OCF₃ H Br OCF₃ Me Br OCHF₂ H Br OCHF₂ Me Br OCH₂CF₃ HBr OCH₂CF₃ Me Br OCF₂CF₃ H Br OCF₂CF₃ Me Br OCF₂CF₂H H Br OCF₂CF₂H Me BrOCHFCF₃ H Br OCHFCF₃ Me Br SCF₃ H Br SCF₃ Me Br SCHF₂ H Br SCHF₂ Me BrSCH₂CF₃ H Br SCH₂CF₃ Me Br SCF₂CF₃ H Br SCF₂CF₃ Me Br SCF₂CF₂H H BrSCF₂CF₂H Me Br SCHFCF₃ H Br SCHFCF₃ Me Br SOCF₃ H Br SOCF₃ Me Br SOCHF₂H Br SOCHF₂ Me Br SOCH₂CF₃ H Br SOCH₂CF₃ Me Br SOCF₂CF₃ H Br SOCF₂CF₃ MeBr SOCF₂CF₂H H Br SOCF₂CF₂H Me Br SOCHFCF₃ H Br SOCHFCF₃ Me Br SO₂CF₃ HBr SO₂CF₃ Me Br SO₂CHF₂ H Br SO₂CHF₂ Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃ MeBr SO₂CF₂CF₃ H Br SO₂CF₂CF₃ Me Br SO₂CF₂CF₂H H Br SO₂CF₂CF₂H Me BrSO₂CHFCF₃ H Br SO₂CHFCF₃ Me Br CN H Br CN Me H Cl Cl Me Cl Cl H Br Cl MeBr Cl H CF₃ Cl Me CF₃ Cl H OCF₃ Cl Me OCF₃ Cl H OCHF₂ Cl Me OCHF₂ Cl HOCH₂CF₃ Cl Me OCH₂CF₃ Cl H OCF₂CF₃ Cl Me OCF₂CF₃ Cl H OCF₂CF₂H Cl MeOCF₂CF₂H Cl H OCHFCF₃ Cl Me OCHFCF₃ Cl H SCF₃ Cl Me SCF₃ Cl H SCHF₂ ClMe SCHF₂ Cl H SCH₂CF₃ Cl Me SCH₂CF₃ Cl H SCF₂CF₃ Cl Me SCF₂CF₃ Cl HSCF₂CF₂H Cl Me SCF₂CF₂H Cl H SCHFCF₃ Cl Me SCHFCF₃ Cl H SOCF₃ Cl MeSOCF₃ Cl H SOCHF₂ Cl Me SOCHF₂ Cl H SOCH₂CF₃ Cl Me SOCH₂CF₃ Cl HSOCF₂CF₃ Cl Me SOCF₂CF₃ Cl H SOCF₂CF₂H Cl Me SOCF₂CF₂H Cl H SOCHFCF₃ ClMe SOCHFCF₃Cl H SO₂CF₃ Cl Me SO₂CF₃ Cl H SO₂CHF₂ Cl Me SO₂CHF₂ Cl HSO₂CH₂CF₃ Cl Me SO₂CH₂CF₃Cl H SO₂CF₂CF₃ Cl Me SO₂CF₂CF₃Cl H SO₂CF₂CF₂HCl Me SO₂CF₂CF₂H Cl H SO₂CHFCF₃ Cl Me SO₂CHFCF₃Cl H CN Cl Me CN Cl T andV are both Cl and U is Me Q R S Q R S Cl Cl H Cl Cl Me Cl Br H Cl Br MeCl CF₃ H Cl CF₃ Me Cl OCF₃ H Cl OCF₃ Me Cl OCHF₂ H Cl OCHF₂ Me ClOCH₂CF₃ H Cl OCH₂CF₃ Me Cl OCF₂CF₃ H Cl OCF₂CF₃ Me Cl OCF₂CF₂H H ClOCF₂CF₂H Me Cl OCHFCF₃ H Cl OCHFCF₃ Me Cl SCF₃ H Cl SCF₃ Me Cl SCHF₂ HCl SCHF₂ Me Cl SCH₂CF₃ H Cl SCH₂CF₃ Me Cl SCF₂CF₃ H Cl SCF₂CF₃ Me ClSCF₂CF₂H H Cl SCF₂CF₂H Me Cl SCHFCF₃ H Cl SCHFCF₃ Me Cl SOCF₃ H Cl SOCF₃Me Cl SOCHF₂ H Cl SOCHF₂ Me Cl SOCH₂CF₃ H Cl SOCH₂CF₃ Me Cl SOCF₂CF₃ HCl SOCF₂CF₃ Me Cl SOCF₂CF₂H H Cl SOCF₂CF₂H Me Cl SOCHFCF₃ H Cl SOCHFCF₃Me Cl SO₂CF₃ H Cl SO₂CF₃ Me Cl SO₂CHF₂ H Cl SO₂CHF₂ Me Cl SO₂CH₂CF₃ H ClSO₂CH₂CF₃ Me Cl SO₂CF₂CF₃ H Cl SO₂CF₂CF₃ Me Cl SO₂CF₂CF₂H H ClSO₂CF₂CF₂H Me Cl SO₂CHFCF₃ H Cl SO₂CIIFCF₃ Me Cl CN H Cl CN Me Cl H ClCl Me Cl Cl H Br Cl Me Br Cl H CF₃ Cl Me CF₃ Cl H OCF₃ Cl Me OCF₃ Cl HOCHF₂ Cl Me OCHF₂ Cl H OCH₂CF₃ Cl Me OCH₂CF₃ Cl H OCF₂CF₂H Cl MeOCF₂CF₂H Cl H SCF₃ Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ Br SCF₃ H Br SCF₃Me Br SCHF₂ H Br SCHF₂ Me Br SCH₂CF₃ H Br SCH₂CF₃ Me Br SCF₂CF₃ H BrSCF₂CF₃ Me Br SCF₂CF₂H H Br SCF₂CF₂H Me Br SCHFCF₃ H Br SCHFCF₃ Me BrSOCF₃ H Br SOCF₃ Me Br SOCHF₂ H Br SOCHF₂ Me Br SOCH₂CF₃ H Br SOCH₂CF₃Me Br SOCF₂CF₃ H Br SOCF₂CF₃Me Br SOCF₂CF₂H H Br SOCF₂CF₂H Me BrSOCHFCF₃ H Br SOCHFCF₃ Me Br SO₂CF₃ H Br SO₂CF₃ Me Br SO₂CHF₂ H BrSO₂CHF₂Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃Me Br SO₂CF₂CF₃ H Br SO₂CF₂CF₃Me BrSO₂CF₂CF₂H H Br SO₂CF₂CF₂H Me Br SO₂CHFCF₃ H Br SO₂CHFCF₃ Me Br CN H BrCN Me H Cl Cl Me Cl Cl H Br Cl Me Br Cl H CF₃ Cl Me CF₃ Cl H OCF₃ Cl MeOCF₃ Cl H OCHF₂ Cl Me OCHF₂ Cl H OCH₂CF₃ Cl Me OCH₂CF₃ Cl H OCF₂CF₃ ClMe OCF₂CF₃ Cl H OCF₂CF₂H Cl Me OCF₂CF₂H Cl H OCHFCF₃ Cl Me OCHFCF₃ Cl HSCF₃ Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ Cl H SCH₂CF₃ Cl Me SCH₂CF₃ Cl HSCF₂CF₃ Cl Me SCF₂CF₃ Cl H SCF₂CF₂H Cl Me SCF₂CF₂H Cl H SCHFCF₃ Cl MeSCHFCF₃ Cl H SOCF₃ Cl Me SOCF₃ Cl H SOCHF₂ Cl Me SOCHF₂ Cl H SOCH₂CF₃ ClMe SOCH₂CF₃ Cl H SOCF₂CF₃ Cl Me SOCF₂CF₃ Cl H SOCF₂CF₂H Cl Me SOCF₂CF₂HCl H SOCHFCF₃ Cl Me SOCHFCF₃ Cl H SO₂CF₃ Cl Me SO₂CF₃ Cl H SO₂CHF₂ Cl MeSO₂CHF₂ Cl H SO₂CH₂CF₃ Cl Me SO₂CH₂CF₃ Cl H SO₂CF₂CF₃ Cl Me SO₂CF₂CF₃ ClH SO₂CF₂CF₂H Cl Me SO₂CF₂CF₂H Cl H SO₂CHFCF₃ Cl Me SO₂CHFCF₃ Cl H CN ClMe CN Cl T is Cl and V and U are both Me Q R S Q R S Cl Cl H Cl Cl Me ClBr H Cl Br Me Cl CF₃ H Cl CF₃ Me Cl OCF₃ H Cl OCF₃ Me Cl OCHF₂ H ClOCHF₂ Me Cl OCH₂CF₃ H Cl OCH₂CF₃ Me Cl OCF₂CF₃ H Cl OCF₂CF₃ Me ClOCF₂CF₂H H Cl OCF₂CF₂H Me Cl OCHFCF₃ H Cl OCHFCF₃ Me Cl SCF₃ H Cl SCF₃Me Cl SCHF₂ H Cl SCHF₂ Me Cl SCH₂CF₃ H Cl SCH₂CF₃ Me Cl SCF₂CF₃ H ClSCF₂CF₃ Me Cl SCF₂CF₂H H Cl SCF₂CF₂H Me Cl SCHFCF₃ H Cl SCHFCF₃ Me ClSOCF₃ H Cl SOCF₃ Me Cl SOCHF₂ H Cl SOCHF₂ Me Cl SOCH₂CF₃ H Cl SOCH₂CF₃Me Cl SOCF₂CF₃ H Cl SOCF₂CF₃ Me Cl SOCF₂CF₂H H Cl SOCF₂CF₂H Me ClSOCHFCF₃ H Cl SOCHFCF₃ Me Cl SO₂CF₃ H Cl SO₂CF₃ Me Cl SO₂CHF₂ H ClSO₂CHF₂ Me Cl SO₂CH₂CF₃ H Cl SO₂CH₂CF₃ Me Cl SO₂CF₂CF₃ H Cl SO₂CF₂CF₃ MeCl SO₂CF₂CF₂H H Cl SO₂CF₂CF₂H Me Cl SO₂CHFCF₃ H Cl SO₂CHFCF₃ Me Cl CN HCl CN Me Cl H Cl Cl Me Cl Cl H Br Cl Me Br Cl H CF3 Cl Me CF3 Cl H OCF3Cl Me OCF3 Cl H OCHF2 Cl Me OCHF2 Cl H OCH2CF3 Cl Me OCH2CF3 Cl HOCF2CF2H Cl Me OCF2CF2H Cl H SCF₃ Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ BrSCF₃ H Br SCF₃ Me Br SCHF₂ H Br SCHF₂ Me Br SCH₂CF₃ H Br SCH₂CF₃ Me BrSCF₂CF₃ H Br SCF₂CF₃ Me Br SCF₂CF₂H H Br SCF₂CF₂H Me Br SCHFCF₃ H BrSCHFCF₃ Me Br SOCF₃ H Br SOCF₃ Me Br SOCHF₂ H Br SOCHF₂ Me Br SOCH₂CF₃ HBr SOCH₂CF₃ Me Br SOCF₂CF₃ H Br SOCF₂CF₃ Me Br SOCF₂CF₂H H Br SOCF₂CF₂HMe Br SOCHFCF₃ H Br SOCHFCF₃ Me Br SO₂CF₃ H Br SO₂CF₃ Me Br SO₂CHF₂ H BrSO₂CHF₂ Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃ Me Br SO₂CF₂CF₃ H Br SO₂CF₂CF₃ MeBr SO₂CF₂CF₂H H Br SO₂CF₂CF₂H Me Br SO₂CHFCF₃ H Br SO₂CHFCF₃ Me Br CN HBr CN Me H Cl Cl Me Cl Cl H Br Cl Me Br Cl H CF₃ Cl Me CF₃ Cl H OCF₃ ClMe OCF₃ Cl H OCHF₂ Cl Me OCHF₂ Cl H OCH₂CF₃ Cl Me OCH₂CF₃ Cl H OCF₂CF₃Cl Me OCF₂CF₃ Cl H OCF₂CF₂H Cl Me OCF₂CF₂H Cl H OCHFCF₃ Cl Me OCHFCF₃ ClH SCF₃ Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ Cl H SCH₂CF₃ Cl Me SCH₂CF₃ Cl HSCF₂CF₃ Cl Me SCF₂CF₃ Cl H SCF₂CF₂H Cl Me SCF₂CF₂H Cl H SCHFCF₃ Cl MeSCHFCF₃ Cl H SOCF₃ Cl Me SOCF₃ Cl H SOCHF₂ Cl Me SOCHF₂ Cl H SOCH₂CF₃ ClMe SOCH₂CF₃ Cl H SOCF₂CF₃ Cl Me SOCF₂CF₃ Cl H SOCF₂CF₂H Cl Me SOCF₂CF₂HCl H SOCHFCF₃ Cl Me SOCHFCF₃ Cl H SO₂CF₃ Cl Me SO₂CF₃ Cl H SO₂CHF₂ Cl MeSO₂CHF₂ Cl H SO₂CH₂CF₃ Cl Me SO₂CH₂CF₃Cl H SO₂CF₂CF₃ Cl Me SO₂CF₂CF₃Cl HSO₂CF₂CF₂H Cl Me SO₂CF₂CF₂H Cl H SO₂CHFCF₃ Cl Me SO₂CHFCF₃ Cl H CN Cl MeCN Cl

[0138] TABLE 9

T and V are both Cl and U is H Q R M Q R M Cl Cl H Cl Cl Me Cl Br H ClBr Me Cl CF₃ H Cl CF₃ Me Cl OCF₃ H Cl OCF₃ Me Cl OCHF₂ H Cl OCHF₂ Me ClOCH₂CF₃ H Cl OCH₂CF₃ Me Cl OCF₂CF₃ H Cl OCF₂CF₃ Me Cl OCF₂CF₂H H ClOCF₂CF₂H Me Cl OCHFCF₃ H Cl OCHFCF₃ Me Cl SCF₃ H Cl SCF₃ Me Cl SCHF₂ HCl SCIIF₂ Me Cl SCH₂CF₃ H Cl SCH₂CF₃ Me Cl SCF₂CF₃ H Cl SCF₂CF₃ Me ClSCF₂CF₂H H Cl SCF₂CF₂H Me Cl SCHFCF₃ H Cl SCHFCF₃ Me Cl SOCF₃ H Cl SOCF₃Me Cl SOCHF₂ H Cl SOCHF₂ Me Cl SOCH₂CF₃ H Cl SOCH₂CF₃ Me Cl SOCF₂CF₃ HCl SOCF₂CF₃ Me Cl SOCF₂CF₂H H Cl SOCF₂CF₂H Me Cl SOCHFCF₃ H Cl SOCHFCF₃Me Cl SO₂CF₃ H Cl SO₂CF₃ Me Cl SO₂CHF₂ H Cl SO₂CHF₂ Me Cl SO₂CH₂CF₃ H ClSO₂CH₂CF₃Me Cl SO₂CF₂CF₃ H Cl SO₂CF₂CF₃Me Cl SO₂CF₂CF₂H H Cl SO₂CF₂CF₂HMe Cl SO₂CHFCF₃ H Cl SO₂CHFCF₃ Me Cl CN H Cl CN Me Cl H Cl Cl Me Cl Cl HBr Cl Me Br Cl H CF₃ Cl Me CF₃ Cl H OCF₃ Cl Me OCF₃ Cl H OCHF₂ Cl MeOCHF₂ Cl H OCH₂CF₃Cl Me OCH₂CF₃ Cl H OCF₂CF₂H Cl Me OCF₂CF₂H Cl H SCF₃Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ Br Cl H Br Cl Me Br Br H Br Br Me BrCF₃ H Br CF₃ Me Br OCF₃ H Br OCF₃ Me Br OCHF₂ H Br OCHF₂ Me Br OCH₂CF₃ HBr OCH₂CF₃ Me Br OCF₂CF₃ H Br OCF₂CF₃ Me Br OCF₂CF₂H H Br OCF₂CF₂H Me BrOCHFCF₃ H Br OCHFCF₃ Me Br SCF₃ H Br SCF₃ Me Br SCHF₂ H Br SCHF₂ Me BrSCH₂CF₃ H Br SCH₂CF₃ Me Br SCF₂CF₃ H Br SCF₂CF₃ Me Br SCF₂CF₂H H BrSCF₂CF₂H Me Br SCHFCF₃ H Br SCHFCF₃ Me Br SOCF₃ H Br SOCF₃ Me Br SOCHF₂H Br SOCHF₂ Me Br SOCH₂CF₃ H Br SOCH₂CF₃ Me Br SOCF₂CF₃ H Br SOCF₂CF₃ MeBr SOCF₂CF₂H H Br SOCF₂CF₂H Me Br SOCHFCF₃ H Br SOCHFCF₃ Me Br SO₂CF₃ HBr SO₂CF₃ Me Br SO₂CHF₂ H Br SO₂CHF₂ Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃ MeBr SO₂CF₂CF₃ H Br SO₂CF₂CF₃Me Br SO₂CF₂CF₂H H Br SO₂CF₂CF₂H Me BrSO₂CHFCF₃ H Br SO₂CHFCF₃ Me Br CN H Br CN Me H Cl Cl Me Cl Cl H Br Cl MeBr Cl H CF₃ Cl Me CF₃ Cl H OCF₃ Cl Me OCF₃ Cl H OCHF₂ Cl Me OCHF₂ Cl HOCH₂CF₃ Cl Me OCH₂CF₃ Cl H OCF₂CF₃ Cl Me OCF₂CF₃ Cl H OCF₂CF₂H Cl MeOCF₂CF₂H Cl H OCHFCF₃ Cl Me OCHFCF₃ Cl H SCF₃ Cl Me SCF₃ Cl H SCHF₂ ClMe SCHF₂ Cl H SCH₂CF₃ Cl Me SCH₂CF₃ Cl H SCF₂CF₃ Cl Me SCF₂CF₃ Cl HSCF₂CF₂H Cl Me SCF₂CF₂H Cl H SCHFCF₃ Cl Me SCHFCF₃ Cl H SOCF₃ Cl MeSOCF₃ Cl H SOCBF₂ Cl Me SOCHF₂ Cl H SOCH₂CF₃ Cl Me SOCH₂CF₃ Cl HSOCF₂CF₃ Cl Me SOCF₂CF₃ Cl H SOCF₂CF₂H Cl Me SOCF₂CF₂H Cl H SOCHFCF₃ ClMe SOCHFCF₃ Cl H SO₂CF₃ Cl Me SO₂CF₃ Cl H SO₂CHF₂ Cl Me SO₂CHF₂ Cl HSO₂CH₂CF₃ Cl Me SO₂CH₂CF₃ Cl H SO₂CF₂CF₃ Cl Me SO₂CF₂CF₃ Cl H SO₂CF₂CF₂HCl Me SO₂CF₂CF₂H Cl H SO₂CHFCF₃ Cl Me SO₂CHFCF₃Cl H CN Cl Me CN Cl T andV are both Cl and U is Me Q R S Q R S Cl Cl H Cl Cl Me Cl Br H Cl Br MeCl CF₃ H Cl CF₃ Me Cl OCF₃ H Cl OCF₃ Me Cl OCHF₂ H Cl OCHF₂ Me ClOCH₂CF₃ H Cl OCH₂CF₃ Me Cl OCF₂CF₃ H Cl OCF₂CF₃ Me Cl OCF₂CF₂H H ClOCF₂CF₂H Me Cl OCHFCF₃ H Cl OCHFCF₃ Me Cl SCF₃ H Cl SCF₃ Me Cl SCHF₂ HCl SCHF₂ Me Cl SCH₂CF₃ H Cl SCH₂CF₃ Me Cl SCF₂CF₃ H Cl SCF₂CF₃ Me ClSCF₂CF₂H H Cl SCF₂CF₂H Me Cl SCHFCF₃ H Cl SCHFCF₃ Me Cl SOCF₃ H Cl SOCF₃Me Cl SOCHF₂ H Cl SOCHF₂ Me Cl SOCH₂CF₃ H Cl SOCH₂CF₃ Me Cl SOCF₂CF₃ HCl SOCF₂CF₃ Me Cl SOCF₂CF₂H H Cl SOCF₂CF₂H Me Cl SOCHFCF₃ H Cl SOCHFCF₃Me Cl SO₂CF₃ H Cl SO₂CF₃ Me Cl SO₂CHF₂ H Cl SO₂CHF₂ Me Cl SO₂CH₂CF₃ H ClSO₂CH₂CF₃ Me Cl SO₂CF₂CF₃ H Cl SO₂CF₂CF₃ Me Cl SO₂CF₂CF₂H H ClSO₂CF₂CF₂H Me Cl SO₂CHFCF₃ H Cl SO₂CHFCF₃ Me Cl CN H Cl CN Me Cl H Cl ClMe Cl Cl H Br Cl Me Br Cl H CF₃ Cl Me CF₃ Cl H OCF₃ Cl Me OCF₃ Cl HOCHF₂ Cl Me OCHF₂ Cl H OCH₂CF₃ Cl Me OCH₂CF₃ Cl H OCF₂CF₂H Cl MeOCF₂CF₂H Cl H SCF₃ Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ Br SCF₃ H Br SCF₃Me Br SCHF₂ H Br SCHF₂ Me Br SCH₂CF₃ H Br SCH₂CF₃ Me Br SCF₂CF₃ H BrSCF₂CF₃ Me Br SCF₂CF₂H H Br SCF₂CF₂H Me Br SCHFCF₃ H Br SCHFCF₃ Me BrSOCF₃ H Br SOCF₃ Me Br SOCHF₂ H Br SOCHF₂ Me Br SOCH₂CF₃ H Br SOCH₂CF₃Me Br SOCF₂CF₃ H Br SOCF₂CF₃ Me Br SOCF₂CF₂H H Br SOCF₂CF₂H Me BrSOCFCF₃ H Br SOCFCF₃CF₃ Me Br SO₂CF₃ H Br SO₂CF₃ Me Br SO₂CHF₂ H BrSO₂CHF₂ Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃ Me Br SO₂CF₂CF₃ H Br SO₂CF₂CF₃ MeBr SO₂CF₂CF₂H H Br SO₂CF₂CF₂H Me Br SO₂CHFCF₃ H Br SO₂CHFCF₃Me Br CN HBr CN Me H Cl Cl Me Cl Cl H Br Cl Me Br Cl H CF₃ Cl Me CF₃ Cl H OCF₃ ClMe OCF₃ Cl H OCHF₂ Cl Me OCHF₂ Cl H OCH₂CF₃ Cl Me OCH₂CF₃ Cl H OCF₂CF₃Cl Me OCF₂CF₃ Cl H OCF₂CF₂H Cl Me OCF₂CF₂H Cl H OCHFCF₃ Cl Me OCHFCF₃ ClH SCF₃ Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ Cl H SCH₂CF₃ Cl Me SCH₂CF₃ Cl HSCF₂CF₃ Cl Me SCF₂CF₃ Cl H SCF₂CF₂H Cl Me SCF₂CF₂H Cl H SCHFCF₃ Cl MeSCHFCF₃ Cl H SOCF₃ Cl Me SOCF₃ Cl H SOCHF₂ Cl Me SOCHF₂ Cl H SOCH₂CF₃ ClMe SOCH₂CF₃ Cl H SOCF₂CF₃ Cl Me SOCF₂CF₃ Cl H SOCF₂CF₂H Cl Me SOCF₂CF₂HCl H SOCHFCF₃ Cl Me SOCHFCF₃Cl H SO₂CF₃ Cl Me SO₂CF₃ Cl H SO₂CHF₂ Cl MeSO₂CHF₂ Cl H SO₂CH₂CF₃ Cl Me SO₂CH₂CF₃ Cl H SO₂CF₂CF₃ Cl Me SO₂CF₂CF₃ ClH SO₂CF₂CF₂H Cl Me SO₂CF₂CF₂H Cl H SO₂CHFCF₃ Cl Me SO₂CHFCF₃ Cl H CN ClMe CN Cl T is Cl and U are both Me Q R S Q R S Cl Cl H Cl Cl Me Cl Br HCl Br Me Cl CF₃ H Cl CF₃ Me Cl OCF₃ H Cl OCF₃ Me Cl OCHF₂ H Cl OCHF₂ MeCl OCH₂CF₃ H Cl OCH₂CF₃ Me Cl OCF₂CF₃ H Cl OCF₂CF₃ Me Cl OCF₂CF₂H H ClOCF₂CF₂H Me Cl OCHFCF₃ H Cl OCHFCF₃ Me Cl SCF₃ H Cl SCF₃ Me Cl SCHF₂ HCl SCHF₂ Me Cl SCH₂CF₃ H Cl SCH₂CF₃ Me Cl SCF₂CF₃ H Cl SCF₂CF₃ Me ClSCF₂CF₂H H Cl SCF₂CF₂H Me Cl SCHFCF₃ H Cl SCHFCF₃ Me Cl SOCF₃ H Cl SOCF₃Me Cl SOCHF₂ H Cl SOCHF₂ Me Cl SOCH₂CF₃ H Cl SOCH₂CF₃ Me Cl SOCF₂CF₃ HCl SOCF₂CF₃ Me Cl SOCF9CF₂H H Cl SOCF₂CF₂H Me Cl SOCHFCF₃ H ClSOCHFCF₃Me Cl SO₂CF₃ H Cl SO₂CF₃ Me Cl SO₂CHF₂ H Cl SO₂CHF₂ Me ClSO₂CH₂CF₃ H Cl SO₂CH₂CF₃Me Cl SO₂CF₂CF₃ H Cl SO₂CF₂CF₃ Me Cl SO₂CF₂CF₂HH Cl SO₂CF₂CF₂H Me Cl SO₂CHFCF₃ H Cl SO₂CHFCF₃ Me Cl CN H Cl CN Me Cl HCl Cl Me Cl Cl H Br Cl Me Br Cl H CF₃ Cl Me CF₃ Cl H OCF₃ Cl Me OCF₃ ClH OCHF₂ Cl Me OCHF₂ Cl H OCH₂CF₃ Cl Me OCH₂CF₃ Cl H OCF₂CF₂H Cl MeOCF₂CF₂H Cl H SCF₃ Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ Br SCF₃ H Br SCF₃Me Br SCHF₂ H Br SCHF₂ Me Br SCH₂CF₃ H Br SCH₂CF₃ Me Br SCF₂CF₃ H BrSCF₂CF₃ Me Br SCF₂CF₂H H Br SCF₂CF₂H Me Br SCHFCF₃ H Br SCHFCF₃ Me BrSOCF₃ H Br SOCF₃ Me Br SOCHF₂ H Br SOCHF₂ Me Br SOCH₂CF₃ H Br SOCH₂CF₃Me Br SOCF₂CF₃ H Br SOCF₂CF₃ Me Br SOCF₂CF₂H H Br SOCF₂CF₂H Me BrSOCHFCF₃ H Br SOCHFCF₃ Me Br SO₂CF₃ H Br SO₂CF₃ Me Br SO₂CHF₂ H BrSO₂CHF₂ Me Br SO₂CH₂CF₃ H Br SO₂CH₂CF₃ Me Br SO₂CF₂CF₃ H Br SO₂CF₂CF₃ MeBr SO₂CF₂CF₂H H Br SO₂CF₂CF₂H Me Br SO₂CHFCF₃ H Br SO₂CHFCF₃ Me Br CN HBr CN Me H Cl Cl Me Cl Cl H Br Cl Me Br Cl H CF₃ Cl Me CF₃ Cl H OCF₃ ClMe OCF₃ Cl H OCHF₂ Cl Me OCHF₂ Cl H OCH₂CF₃ Cl Me OCH₂CF₃ Cl H OCF₂CF₃Cl Me OCF₂CF₃ Cl H OCF₂CF₂H Cl Me OCF₂CF₂H Cl H OCHFCF₃ Cl Me OCHFCF₃ ClH SCF₃ Cl Me SCF₃ Cl H SCHF₂ Cl Me SCHF₂ Cl H SCH₂CF₃ Cl Me SCH₂CF₃ Cl HSCF₂CF₃ Cl Me SCF₂CF₃ Cl H SCF₂CF₂H Cl Me SCF₂CF₂H Cl H SCHFCF₃ Cl MeSCHFCF₃ Cl H SOCF₃ Cl Me SOCF₃ Cl H SOCHF₂ Cl Me SOCHF₂ Cl H SOCH₂CF₃ ClMe SOCH₂CF₃ Cl H SOCF₂CF₃ Cl Me SOCF₂CF₃ Cl H SOCF₂CF₂H Cl Me SOCF₂CF₂HCl H SOCHFCF₃ Cl Me SOCHFCF₃ Cl H SO₂CF₃ Cl Me SO₂CF₃ Cl H SO₂CHF₂ Cl MeSO₂CHF₂ Cl H SO₂CH₂CF₃ Cl Me SO₂CH₂CF₃ Cl H SO₂CF₂CF₃ Cl Me SO₂CF₂CF₃ ClH SO₂CF₂CF₂H Cl Me SO₂CF₂CF₂H Cl H SO₂CHFCF₃ Cl Me SO₂CHFCF₃ Cl H CN ClMe CN Cl

[0139] TABLE 10

R R² U R R² U I H H I H Me OCHF₂ H H OCHF₂ H Me OCH₂F H H OCH₂F H MeOCF₂Cl H H OCF₂Cl H Me OCH₂CF₃ H H OCH₂CF₃ H Me Et H H Et H Me CN H H CNH Me NH₂ H H NH₂ H Me NHCOMe H H NHCOMe H Me NHCOCF₃ H H NHCOCF₃ H MeSCF₃ H H SCF₃ H Me SCHF₂ H H SCHF₂ H Me SCH₂F H H SCH₂F H Me Ph H H Ph HMe Me₃Si H H Me₃Si H Me I Me H I Me Me OCHF₂ Me H OCHF₂ Me Me OCH₂F Me HOCH₂F Me Me OCF₂Cl Me H OCF₂Cl Me Me OCH₂CF₃ Me H OCH₂CF₃ Me Me Et Me HEt Me Me CN Me H CN Me Me NH₂ Me H NH₂ Me Me NHCOMe Me H NHCOMe Me MeNHCOCF₃ Me H NHCOCF₃ Me Me SCF₃ Me H SCF₃ Me Me SCHF₂ Me H SCHF₂ Me MeSCH₂F Me H SCH₂F Me Me Ph Me H Ph Me Me Me₃Si Me H Me₃Si Me Me

[0140] TABLE 11

Q R² U Q R² U I H H I H Me OCHF₂ H H OCHF₂ H Me OCH₂F H H OCH₂F H MeOCF₂Cl H H OCF₂Cl H Me OCH₂CF₃ H H OCH₂CF₃ H Me Et H H Et H Me CN H H CNH Me NH₂ H H NH₂ H Me NHCOMe H H NHCOMe H Me NHCOCF₃ H H NHCOCF₃ H MeSCF₃ H H SCF₃ H Me SCHF₂ H H SCHF₂ H Me SCH₂F H H SCH₂F H Me Ph H H Ph HMe Me₃Si H H Me₃Si H Me I Me H I Me Me OCHF₂ Me H OCHF₂ Me Me OCH₂F Me HOCH₂F Me Me OCF₂Cl Me H OCF₂Cl Me Me OCH₂CF₃ Me H OCH₂CF₃ Me Me Et Me HEt Me Me CN Me H CN Me Me NH₂ Me H NH₂ Me Me NHCOMe Me H NHCOMe Me MeNHCOCF₃ Me H NHCOCF₃ Me Me SCF₃ Me H SCF₃ Me Me SCHF₂ Me H SCHF₂ Me MeSCH₂F Me H SCH₂F Me Me Ph Me H Ph Me Me Me₃Si Me H Me₃Si Me Me

[0141] TABLE 12

Q R² U Q R² U I H H I H Me OCHF₂ H H OCHF₂ H Me OCH₂F H H OCH₂F H MeOCF₂Cl H H OCF₂Cl H Me OCH₂CF₃ H H OCH₂CF₃ H Me Et H H Et H Me CN H H CNH Me NH₂ H H NH₂ H Me NHCOMe H H NHCOMe H Me NHCOCF₃ H H NHCOCF₃ H MeSCF₃ H H SCF₃ H Me SCHF₂ H H SCHF₂ H Me SCH₂F H H SCH₂F H Me Ph H H Ph HMe Me₃Si H H Me₃Si H Me I Me H I Me Me OCHF₂ Me H OCHF₂ Me Me OCH₂F Me HOCH₂F Me Me OCF₂Cl Me H OCF₂Cl Me Me OCH₂CF₃ Me H OCH₂CF₃ Me Me Et Me HEt Me Me CN Me H CN Me Me NH₂ Me H NH₂ Me Me NHCOMe Me H NHCOMe Me MeNHCOCF₃ Me H NHCOCF₃ Me Me SCF₃ Me H SCF₃ Me Me SCHF₂ Me H SCHF₂ Me MeSCH₂F Me H SCH₂F Me Me Ph Me H Ph Me Me Me₃Si Me H Me₃Si Me Me

[0142] Formulation/Utility

[0143] Compounds of this invention will generally be used as aformulation or composition with an agriculturally suitable carriercomprising at least one of a liquid diluent, a solid diluent or asurfactant. The formulation or composition ingredients are selected tobe consistent with the physical properties of the active ingredient,mode of application and environmental factors such as soil type,moisture and temperature. Useful formulations include liquids such assolutions (including emulsifiable concentrates), suspensions, emulsions(including microemulsions and/or suspoemulsions) and the like whichoptionally can be thickened into gels. Useful formulations furtherinclude solids such as dusts, powders, granules, pellets, tablets,films, and the like which can be water-dispersible (“wettable”) orwater-soluble. Active ingredient can be (micro)encapsulated and furtherformed into a suspension or solid formulation; alternatively the entireformulation of active ingredient can be encapsulated (or “overcoated”).Encapsulation can control or delay release of the active ingredient.Sprayable formulations can be extended in suitable media and used atspray volumes from about one to several hundred liters per hectare.High-strength compositions are primarily used as intermediates forfurther formulation.

[0144] The formulations will typically contain effective amounts (e.g.from 0.01-99.99 weight percent) of active ingredient together withdiluent and/or surfactant within the following approximate ranges whichadd up to 100 percent by weight. Weight Percent Active IngredientDiluent Surfactant Water-Dispersible and Water-  5-90 0-94 1-15 solubleGranules, Tablets and Powders. Suspensions, Emulsions, Solutions  5-5040-95  0-25 (including Emulsifiable Concentrates and SuspensionConcentrates) Dusts  1-25 70-99  0-5  Granules and Pellets 0.01-99    5-99.99 0-15 High Strength Compositions 90-99 0-10 0-2 

[0145] Typical solid diluents are described in Watkins, et al., Handbookof Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books,Caldwell, N.J. Typical liquid diluents are described in Marsden,Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon'sDetergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, N.J.,as well as Sisely and Wood, Encyclopedia of Surface Active Agents,Chemical Publ. Co., Inc., New York, 1964, list surfactants andrecommended uses. All formulations can contain minor amounts ofadditives to reduce foam, caking, corrosion, microbiological growth andthe like, or thickeners to increase viscosity.

[0146] Surfactants include, for example, polyethoxylated alcohols,polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acidesters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzenesulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates,naphthalene sulfonate formaldehyde condensates, polycarboxylates, andpolyoxyethylene/polyoxypropylene block copolymers. Solid diluentsinclude, for example, clays such as bentonite, montmorillonite,attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth,urea, calcium carbonate, sodium carbonate and bicarbonate, and sodiumsulfate. Liquid diluents include, for example, water,N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethyleneglycol, polypropylene glycol, paraffins, alkylbenzenes,allylnaphthalenes, oils of olive, castor, linseed, twig, sesame, corn,peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters,ketones such as cyclohexanone, 2-heptanone, isophorone and4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol,cyclohexanol, decanol and tetrahydrofurfuryl alcohol.

[0147] Solutions, including emulsifiable concentrates, can be preparedby simply mixing the ingredients. Dusts and powders can be prepared byblending and, usually, grinding as in a hammer mill or fluid-energymill. Suspensions are usually prepared by wet-milling; see, for example,U.S. Pat. No. 3,060,084. Preferred suspension concentrates include thosecontaining, in addition to the active ingredient, from 5 to 20% nonionicsurfactant (for example, polyethoxylated fatty alcohols) optionallycombined with 50-65% liquid diluents and up to 5% anionic surfactants.Granules and pellets can be prepared by spraying the active materialupon preformed granular carriers or by agglomeration techniques. SeeBrowning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp147-48, Perry's Chemical Enigineer's Handbook, 4th Ed., McGraw-Hill, NewYork, 1963, pages 8-57 and following, and WO 91/13546. Pellets can beprepared as described in U.S. Pat. No. 4,172,714. Water-dispersible andwater-soluble granules can be prepared as taught in U.S. Pat. No.4,144,050, U.S. Pat. No. 3,920,442 and DE 3,246,493. Tablets can beprepared as taught in U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701and U.S. Pat. No. 5,208,030. Films can be prepared as taught in GB2,095,558 and U.S. Pat. No. 3,299,566.

[0148] For further information regarding the art of formulation, seeU.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 andExamples 10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7,line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140,162-164, 166, 167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as aScience, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hanceet al., Weed Control Handbook, 8th Ed., Blackwell ScientificPublications, Oxford, 1989.

[0149] In the following Examples, all percentages are by weight and allformulations are prepared in conventional ways. Compound numbers referto compounds in Index Tables A-D.

EXAMPLE A

[0150] Wettable Powder Compound 8 65.0% dodecylphenol polyethyleneglycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate6.0% montmorillonite (calcined) 23.0%.

EXAMPLE B

[0151] Granule Compound 8 10.0% attapulgite granules (low volatilematter, 90.0%. 0.71/0.30 mm; U.S.S. No. 25-50 sieves)

EXAMPLE C

[0152] Extruded Pellet Compound 8 25.0% anhydrous sodium sulfate 10.0%crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0%calcium/magnesium bentonite 59.0%.

EXAMPLE D

[0153] Emulsifiable Concentrate Compound 8 20.0% blend of oil solublesulfonates 10.0% and polyoxyethylene ethers isophorone 70.0%.

[0154] Of note are suspension concentrates comprising 15-25% activeingredient, 10-20% nonionic surfactants, 0-5% anionic surfactants, 0-10%organic diluents, and 45-60% water.

EXAMPLE E

[0155] Compound 2 20.0% polyethoxylated fatty alcohol nonionicsurfactant 15.0% ester derivative of montan wax 3.0% calciumlignosulfonate anionic surfactant 2.0% polyethoxylated/polypropoxylatedpolyglycol block copolymer surfactant 1.0% propylene glycol diluent 6.4%poly(dimethylsiloxane) antifoam agent 0.6% antimicrobial agent 0.1%water diluent 51.9%

[0156] The formulation ingredients are mixed together as a syrup,Compound 2 is added and the mixture is homogenized in a blender. Theresulting slurry is then wet-milled to form a suspension concentrate.

EXAMPLE F

[0157] Compound 5 20.0% polyethoxylated fatty alcohol nonionicsurfactant 15.0% ester derivative of montan wax 3.0% calciumlignosulfonate anionic surfactant 2.0% polyethoxylated/polypropoxylatedpolyglycol block copolymer surfactant 1.0% propylene glycol diluent 6.4%poly(dimethylsiloxane) antifoam agent 0.6% antimicrobial agent 0.1%water diluent 51.9%

[0158] The formulation ingredients are mixed together as a syrup,Compound 5 is added and the mixture is homogenized in a blender. Theresulting slurry is then wet-milled to form a suspension concentrate.

EXAMPLE G

[0159] Compound 8 20.0% polyethoxylated fatty alcohol nonionicsurfactant 15.0% ester derivative of montan wax 3.0% calciumlignosulfonate anionic surfactant 2.0% polyethoxylated/polypropoxylatedpolyglycol block copolymer surfactant 1.0% propylene glycol diluent 6.4%poly(dimethylsiloxane) antifoam agent 0.6% antimicrobial agent 0.1%water diluent 51.9%

[0160] The formulation ingredients are mixed together as a syrup,Compound 8 is added and the mixture is homogenized in a blender. Theresulting slurry is then wet-milled to form a suspension concentrate.

EXAMPLE H

[0161] Compound 28 20.0% polyethoxylated fatty alcohol nonionicsurfactant 15.0% ester derivative of montan wax 3.0% calciumlignosulfonate anionic surfactant 2.0% polyethoxylated/polypropoxylatedpolyglycol block copolymer surfactant 1.0% propylene glycol diluent 6.4%poly(dimethylsiloxane) antifoam agent 0.6% antimicrobial agent 0.1%water diluent 51.9%

[0162] The formulation ingredients are mixed together as a syrup,Compound 28 is added and the mixture is homogenized in a blender. Theresulting slurry is then wet-milled to form a suspension concentrate.

EXAMPLE I

[0163] Compound 29 20.0% polyethoxylated fatty alcohol nonionicsurfactant 15.0% ester derivative of montan wax 3.0% calciumlignosulfonate anionic surfactant 2.0% polyethoxylated/polypropoxylatedpolyglycol block copolymer surfactant 1.0% propylene glycol diluent 6.4%poly(dimethylsiloxane) antifoam agent 0.6% antimicrobial agent 0.1%water diluent 51.9%

[0164] The formulation ingredients are mixed together as a syrup,Compound 29 is added and the mixture is homogenized in a blender. Theresulting slurry is then wet-milled to form a suspension concentrate.

EXAMPLE J

[0165] Compound 30 20.0% polyethoxylated fatty alcohol nonionicsurfactant 15.0% ester derivative of montan wax 3.0% calciumlignosulfonate anionic surfactant 2.0% polyethoxylated/polypropoxylatedpolyglycol block copolymer surfactant 1.0% propylene glycol diluent 6.4%poly(dimethylsiloxane) antifoam agent 0.6% antimicrobial agent 0.1%water diluent 51.9%

[0166] The formulation ingredients are mixed together as a syrup,Compound 30 is added and the mixture is homogenized in a blender. Theresulting slurry is then wet-milled to form a suspension concentrate.

EXAMPLE K

[0167] Compound 31 20.0% polyethoxylated fatty alcohol nonionicsurfactant 15.0% ester derivative of montan wax 3.0% calciumlignosulfonate anionic surfactant 2.0% polyethoxylated/polypropoxylatedpolyglycol block copolymer surfactant 1.0% propylene glycol diluent 6.4%poly(dimethylsiloxane) antifoam agent 0.6% antimicrobial agent 0.1%water diluent 51.9%

[0168] The formulation ingredients are mixed together as a syrup,Compound 31 is added and the mixture is homogenized in a blender. Theresulting slurry is then wet-milled to form a suspension concentrate.

EXAMPLE L

[0169] Compound 35 20.0% polyethoxylated fatty alcohol nonionicsurfactant 15.0% ester derivative of montan wax 3.0% calciumlignosulfonate anionic surfactant 2.0% polyethoxylated/polypropoxylatedpolyglycol block copolymer surfactant 1.0% propylene glycol diluent 6.4%poly(dimethylsiloxane) antifoam agent 0.6% antimicrobial agent 0.1%water diluent 51.9%

[0170] The formulation ingredients are mixed together as a syrup,Compound 35 is added and the mixture is homogenized in a blender. Theresulting slurry is then wet-milled to form a suspension concentrate.

EXAMPLE M

[0171] Compound 36 20.0% polyethoxylated fatty alcohol nonionicsurfactant 15.0% ester derivative of montan wax 3.0% calciumlignosulfonate anionic surfactant 2.0% polyethoxylated/polypropoxylatedpolyglycol block copolymer surfactant 1.0% propylene glycol diluent 6.4%poly(dimethylsiloxane) antifoam agent 0.6% antimicrobial agent 0.1%water diluent 51.9%

[0172] The formulation ingredients are mixed together as a syrup,Compound 35 is added and the mixture is homogenized in a blender. Theresulting slurry is then wet-milled to form a suspension concentrate.

EXAMPLE N

[0173] Compound 37 20.0% polyethoxylated fatty alcohol nonionicsurfactant 15.0% ester derivative of montan wax 3.0% calciumlignosulfonate anionic surfactant 2.0% polyethoxylated/polypropoxylatedpolyglycol block copolymer surfactant 1.0% propylene glycol diluent 6.4%poly(dimethylsiloxane) antifoam agent 0.6% antimicrobial agent 0.1%water diluent 51.9%

[0174] The formulation ingredients are mixed together as a syrup,Compound 35 is added and the mixture is homogenized in a blender. Theresulting slurry is then wet-milled to form a suspension concentrate.

[0175] The compounds of this invention are useful as plant diseasecontrol agents. The present invention therefore further comprises amethod for controlling plant diseases caused by frugal plant pathogenscomprising applying to the plant or portion thereof to be protected, orto the plant seed or seedling to be protected, an effective amount of acompound of the invention or a fungicidal composition containing saidcompound. The compounds and compositions of this invention providecontrol of diseases caused by a broad spectrum of fungal plant pathogensin the Basidiomycete, Ascomycete, Oomycete and Deuteromycete classes.They are effective in controlling a broad spectrum of plant diseases,particularly foliar pathogens of ornamental, vegetable, field, cereal,and fruit crops. These pathogens include Plasmopara viticola,Phytophthora infestans, Peronospora tabacina, Pseudoperonosporacubensis, Pythium aphanidermatum, Alternaria brassicae, Septorianodorum, Septoria tritici, Cercosporidium personatum, Cercosporaarachidicola, Pseudocercosporella herpotrichoides, Cercospora beticola,Botrytis cinerea, Monilinia fructicola, Pyricularia oryzae, Podosphaeraleucotricha, Venturia inaequalis, Erysiphe graminis, Uncinula necatur,Puccinia recondita, Puccinia graminis, Hemileia vastatrix, Pucciniastriiformis, Puccinia arachidis, Rhizoctonia solani, Sphaerothecafuliginea, Fusarium oxysporum, Verticillium dahliae, Pythiumaphanidermatum, Phytophthora megasperma, Sclerotinia sclerotiorum,Sclerotium rolfsii, Eysiphe polygoni, Pyrenophora teres, Gaeunannomycesgraminis, Rynchosporium secalis, Fusarium roseum, Bremia lactucae andother generea and species closely related to these pathogens.

[0176] Compounds of this invention can also be mixed with one or moreother insecticides, fungicides, nematocides, bactericides, acaricides,growth regulators, chemosterilants, semiochemicals, repellents,attractants, pheromones, feeding stimulants or other biologically activecompounds to form a multi-component pesticide giving an even broaderspectrum of agricultural protection. Examples of such agriculturalprotectants with which compounds of this invention can be formulatedare: insecticides such as abamectin, acephate, azinphos-methyl,bifenthrin, buprofezin, carbofuran, chlorfenapyr, chlorpyrifos,chlorpyrifos-methyl, cyfluthrin, beta-cyfluthrin, cyhalothnin,lambda-cyhalothrin, deltamethrin, diafenthiuron, diazinon,diflubenzuron, dimethoate, esfenvalerate, fenoxycarb, fenpropathrin,fenvalerate, fipronil, flucythrinate, tau-fluvalinate, fonophos,imidacloprid, isofeuphos, malathion, metaldehyde, methamidophos,methidathion, methomyl, methoprene, methoxychlor, methyl7-chloro-2,5-dihydro-2-[[N-(methoxycarbonyl)-N-[4-(trifluoromethoxy)phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylate(indoxacarb), monocrotophos, oxamyl, parathion, parathion-methyl,permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb,profenofos, rotenone, sulprofos, tebufenozide, tefluthrin, terbufos,tetrachlorvinphos, thiodicarb, tralomethrin, trichlorfon andtriflumuron; fiugicides such as acibenzolar, azoxystrobin, benomyl,blasticidin-S, Bordeaux mixture (tribasic copper sulfate),bromuconazole, carpropamid (KTU 3616), captafol, captan, carbendazim,chloroneb, chlorothalonil, copper oxychloride, copper salts such ascopper sulfate and copper hydroxide, cyazofamid, cymoxanil,cyproconazole, cyprodinil (CGA 219417),(S)-3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide(RH 7281), diclocymet (S-2900), diclomezine, dicloran, difenoconazole,dimethomorph, diniconazole, diniconazole-M, dodine, edifenphos,epoxiconazole (BAS 480F), famoxadone, fenamidone, fenarimol,fenbuconazole, fencaramid (SZX0722), fenpiclonil, fenpropidin,fenpropimorph, fentin acetate, fentin hydroxide, fluazinam, fludioxonil,flumetover (RPA 403397), fluquinconazole, flusilazole, flutolanil,flutriafol, folpet, fosetyl-aluminum, firalaxyl, furametapyr (S-82658),hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane,iprovalicarb, kasugamycin, kresoxim-methyl, mancozeb, maneb, mefenoxam,mepronil, metalaxyl, metconazole, metominostrobin/fenominostrobin(SSF-126), myclobutanil, neo-asozin (ferric methanearsonate), oxadixyl,penconazole, pencycuron, probenazole, prochloraz, propamocarb,propiconazole, propineb, pyrclostrobin, pyrifenox, pyrimethanil,pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole,tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram,triadimefon, triadimenol, tricyclazole, trifloxystrobin, triticonazole,validamycin, vinclozolin, zineb and zoxamid; nematocides such asaldoxycarb and fenamiphos; bactericides such as streptomycin; acaricidessuch as amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol,dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathriu,fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; andbiological agents such as Bacillus thuringiensis, Bacillusthuringiensisdelta endotoxin, baculovirus, and entomopathogenicbacteria, virus and fungi. The weight ratios of these various mixingpartners to compounds of this invention typically are between 100:1 and1:100, preferably between 30:1 and 1:30, more preferably between 10:1and 1:10 and most preferably between 4:1 and 1:4.

[0177] Of note are combinations with other fungicides giving an evenbroader spectrum of agricultural protection including azoxystrobin,kresoxim-methyl, pyrclostrobin, trifloxystrobin, benomyl, carbendazim,chlorothalonil, dimethomorph, folpet, mancozeb, maneb, quinoxyfen,validamycin, vinclozolin, fenpropidine, fenpropimorph, bromuconazole,cyproconazole, difenoconazole, epoxyconazole, flusilazole, ipconazole,metconazole, propiconazole, tebuconazole and triticonazole.

[0178] Of note are combinations with other fungicides of a differentmode of action (e.g. mitochondrial respiration inhibition, inhibition ofprotein synthesis by interference of the synthesis of ribosomal RNA orinhibition of beta-tubulin synthesis) that can be particularlyadvantageous for resistance management. Examples include combinations ofcompounds of Formula I and/or Formula II (e.g. Compound 8) withazoxystrobin, kresoxim-methyl, pyrclostrobin, trifloxystrobin,carbendazim, famoxadone, fenamidone, benomyl, cymoxanil, dimethomorph,folpet, fosetyl-aluminum, metalaxyl, mancozeb, maneb. These combinationscan be particularly advantageous for resistance management, especiallywhere the fungicides of the combination control the same or similardiseases.

[0179] Of note are combinations with other fungicides for controllinggrape diseases including dithiocarbamates such as mancozeb, maneb,propineb and zineb, phthalimids such as folpet, copper salts such ascopper sulfate and copper hydroxide, strobilurins such as azoxystrobin,pyrclostrobin and trifloxystrobin, phenylamides such as metalaxyl,phosphonates such as fosetyl-Al, morpholines such as dimethomorph, andother fungicides such as cymoxanil, famoxadone and fenamidone.

[0180] Of note are combinations with other fungicides for controllingpotato diseases including dithiocarbamates such as mancozeb, maneb,propineb and zineb, copper salts such as copper sulfate and copperhydroxide, strobilurins such as pyrclostrobin and trifloxystrobin,phenylamides such as metalaxyl, carbamates such as propamocarb,phenylpyriylamines such as fluazinam, morpholines such as dimethomorph,and other fungicides such as chlorothalonil, cyazofamid, cymoxanil,famoxadone, fenamidone, zoxamid and iprovalicarb.

[0181] Of particular note are combinations of Compound 2, Compound 5,Compound 8, Compound 28, Compound 29, Compound 30, Compound 31, Compound35, Compound 36 or Compound 37 with azoxystrobin, combinations ofCompound 2, Compound 5, Compound 8, Compound 28, Compound 29, Compound30, Compound 31, Compound 35, Compound 36 or Compound 37 withkresoxim-methyl, combinations of Compound 2, Compound 5, Compound 8,Compound 28, Compound 29, Compound 30, Compound 31, Compound 35,Compound 36 or Compound 37 with pyrclostrobin, combinations of Compound2, Compound 5, Compound 8, Compound 28, Compound 29, Compound 30,Compound 31, Compound 35, Compound 36 or Compound 37 withtrifloxystrobin, combinations of Compound 2, Compound 5, Compound 8,Compound 28, Compound 29, Compound 30, Compound 31, Compound 35,Compound 36 or Compound 37 with carbendazim, combinations of Compound 2,Compound 5, Compound 8, Compound 28, Compound 29, Compound 30, Compound31, Compound 35, Compound 36 or Compound 37 with chlorothalonil,combinations of Compound 2, Compound 5, Compound 8, Compound 28,Compound 29, Compound 30, Compound 31, Compound 35, Compound 36 orCompound 37 with dimethomorph, combinations of Compound 2, Compound 5,Compound 8, Compound 28, Compound 29, Compound 30, Compound 31, Compound35, Compound 36 or Compound 37 with folpet, combinations of Compound 2,Compound 5, Compound 8, Compound 28, Compound 29, Compound 30, Compound31, Compound 35, Compound 36 or Compound 37 with mancozeb, combinationsof Compound 2, Compound 5, Compound 8, Compound 28, Compound 29,Compound 30, Compound 31, Compound 35, Compound 36 or Compound 37 withmaneb, combinations of Compound 2, Compound 5, Compound 8, Compound 28,Compound 29, Compound 30, Compound 31, Compound 35, Compound 36 orCompound 37 with quinoxyfen, combinations of Compound 2, Compound 5,Compound 8, Compound 28, Compound 29, Compound 30, Compound 31, Compound35, Compound 36 or Compound 37 with validamycin, combinations ofCompound 2, Compound 5, Compound 8, Compound 28, Compound 29, Compound30, Compound 31, Compound 35, Compound 36 or Compound 37 withvinclozolin, Compound 2, Compound 5, Compound 8, Compound 28, Compound29, Compound 30, Compound 31, Compound 35, Compound 36 or Compound 37with fenpropidine, Compound 2, Compound 5, Compound 8, Compound 28,Compound 29, Compound 30, Compound 31, Compound 35, Compound 36 orCompound 37 with fenpropimorph, Compound 2, Compound 5, Compound 8,Compound 28, Compound 29, Compound 30, Compound 31, Compound 35,Compound 36 or Compound 37 with bromuconazole, Compound 2, Compound 5,Compound 8, Compound 28, Compound 29, Compound 30, Compound 31, Compound35, Compound 36 or Compound 37 with cyproconazole, Compound 2, Compound5, Compound 8, Compound 28, Compound 29, Compound 30, Compound 31,Compound 35, Compound 36 or Compound 37 with difenoconazole, Compound 2,Compound 5, Compound 8, Compound 28, Compound 29, Compound 30, Compound31, Compound 35, Compound 36 or Compound 37 with epoxyconazole, Compound2, Compound 5, Compound 8, Compound 28, Compound 29, Compound 30,Compound 31, Compound 35, Compound 36 or Compound 37 with flusilazole,Compound 2, Compound 5, Compound 8, Compound 28, Compound 29, Compound30, Compound 31, Compound 35, Compound 36 or Compound 37 withipconazole, Compound 2, Compound 5, Compound 8, Compound 28, Compound29, Compound 30, Compound 31, Compound 35, Compound 36 or Compound 37with metconazole, Compound 2, Compound 5, Compound 8, Compound 28,Compound 29, Compound 30, Compound 31, Compound 35, Compound 36 orCompound 37 with propiconazole, Compound 2, Compound 5, Compound 8,Compound 28, Compound 29, Compound 30, Compound 31, Compound 35,Compound 36 or Compound 37 with tebuconazole, Compound 2, Compound 5,Compound 8, Compound 28, Compound 29, Compound 30, Compound 31, Compound35, Compound 36 or Compound 37 with triticonazole, Compound 2, Compound5, Compound 8, Compound 28, Compound 29, Compound 30, Compound 31,Compound 35, Compound 36 or Compound 37 with famoxadone, Compound 2,Compound 5, Compound 8, Compound 28, Compound 29, Compound 30, Compound31, Compound 35, Compound 36 or Compound 37 with fenamidone, Compound 2,Compound 5, Compound 8, Compound 28, Compound 29, Compound 30, Compound31, Compound 35, Compound 36 or Compound 37 with benomyl, Compound 2,Compound 5, Compound 8, Compound 28, Compound 29, Compound 30, Compound31, Compound 35, Compound 36 or Compound 37 with cymoxanil, Compound 2,Compound 5, Compound 8, Compound 28, Compound 29, Compound 30, Compound31, Compound 35, Compound 36 or Compound 37 with dimethomorph, Compound2, Compound 5, Compound 8, Compound 28, Compound 29, Compound 30,Compound 31, Compound 35, Compound 36 or Compound 37 with folpet,Compound 2, Compound 5, Compound 8, Compound 28, Compound 29, Compound30, Compound 31, Compound 35, Compound 36 or Compound 37 withfosetyl-aluminum, Compound 2, Compound 5, Compound 8, Compound 28,Compound 29, Compound 30, Compound 31, Compound 35, Compound 36 orCompound 37 with metalaxyl, Compound 2, Compound 5, Compound 8, Compound28, Compound 29, Compound 30, Compound 31, Compound 35, Compound 36 orCompound 37 with Compound 2, Compound 5, Compound 8, Compound 28,Compound 29, Compound 30, Compound 31, Compound 35, Compound 36 orCompound 37 with propineb, Compound 2, Compound 5, Compound 8, Compound28, Compound 29, Compound 30, Compound 31, Compound 35, Compound 36 orCompound 37 with zineb, Compound 2, Compound 5, Compound 8, Compound 28,Compound 29, Compound 30, Compound 31, Compound 35, Compound 36 orCompound 37 with copper sulfate, Compound 2, Compound 5, Compound 8,Compound 28, Compound 29, Compound 30, Compound 31, Compound 35,Compound 36 or Compound 37 with copper hydroxide, Compound 2, Compound5, Compound 8, Compound 28, Compound 29, Compound 30, Compound 31,Compound 35, Compound 36 or Compound 37 with propamocarb, Compound 2,Compound 5, Compound 8, Compound 28, Compound 29, Compound 30, Compound31, Compound 35, Compound 36 or Compound 37 with cyazofamid, Compound 2,Compound 5, Compound 8, Compound 28, Compound 29, Compound 30, Compound31, Compound 35, Compound 36 or Compound 37 with zoxamid and Compound 2,Compound 5, Compound 8, Compound 28, Compound 29, Compound 30, Compound31, Compound 35, Compound 36 or Compound 37 with iprovalicarb.

[0182] Plant disease control is ordinarily accomplished by applying aneffective amount of a compound of this invention either pre- orpost-infection, to the portion of the plant to be protected such as theroots, stems, foliage, fruit, seeds, tubers or bulbs, or to the media(soil or sand) in which the plants to be protected are growing. Thecompounds can also be applied to the seed to protect the seed andseedling.

[0183] Rates of application for these compounds can be influenced bymany factors of the environment and should be determined under actualuse conditions. Foliage can normally be protected when treated at a rateof from less than 1 g/ha to 5,000 g/ha of active ingredient. Seed andseedlings can normally be protected when seed is treated at a rate offrom 0.1 to 10 g per kilogram of seed.

[0184] The following TESTS demonstrate the control efficacy of compoundsof this invention on specific pathogens. The pathogen control protectionafforded by the compounds is not limited, however, to these species. SeeIndex Tables A-E for compound descriptions. The following abbreviationsare used in the Index Tables that follow: Me is methyl, Et is ethyl, Phis phenyl, OMe is methoxy, OEt is ethoxy. The abbreviation “dec”indicates that the compound appeared to decompose on melting. Theabbreviation “Ex.” stands for “Example” and is followed by a numberindicating in which example the compound is prepared. INDEX TABLE A

Compound Number (R⁵)_(m) (R⁶)_(m) m.p. (° C.) 1 3-Cl-5-CF₃ 3-Cl 108-1092 3-Cl-5-CF₃ 3-Cl-5-Me 3 3-Cl-5-CF₃ 3-OH

[0185] INDEX TABLE B

Compound Number R¹ R² (R⁵)_(m) (R⁶)_(p) m.p. (° C.)  4 H H 3-Cl-5-CF₃2,6-Cl₂ 110-111  5 H H 3-Cl-5-CF₃ 2-Cl *  6 H H 3-Cl-5-CF₃ 6-Cl  7 H H3-Cl-5-CF₃ 5,6-Cl₂ * 8 (Ex. 1) H H 3-Cl-5-CF₃ 2,4-Cl₂-6-Me *  9 H H3-Cl-5-CF₃ 2-NH₂ 10 H H 3-Cl-5-CF₃ 5-Br 11 H H 3-Cl-5-CF₃ 2-OH 12 H H3-Cl-5-CF₃ 2-OMe 13 H H 3-Cl-5-CF₃ 2-OEt 14 H H 3-Cl-5-CF₃ 2-Cl-6-Me 15H H 3-Cl-5-CF₃ 2-OPh 16 H H 3-Cl-5-CF₃ 2-SPh 17 H H 3-Cl-5-CF₃ 5-C≡C-Ph18 H H 3-Cl-5-CF₃ 2-Br-6-CF₃ * 19 H H 3-Cl-5-CF₃ 2-OH-6-Me * 20 H H3-Cl-5-CF₃ 2-Me-6-CF₃ * 21 H H 3-Cl-5-CF₃ 2-Me-6-CF₂CF₃ * 22 H H3-Cl-5-CF₃ 2-OMe-6-CF₃ * 23 H H 3-Cl-5-CF₃ 2-CH₂OMe-6-CF₃ * 24 H H3-Cl-5-CF₃ 2-Ph-6-CF₃ * 25 H H 3-Cl-5-CF₃ 2-Me-6-Cl * 26 H H 3-Cl-5-CF₃6-CF₃ * 27 H H 3-Cl-5-CF₃ 2-NH—C₆H₄(3-CF₃) * 28 (Ex. 2) H H 3-Cl-5-CF₃2,4-Cl₂ 122-124 29 H H 3-Cl-5-CF₃ 2,4-Cl₂-5-Me * 30 (Ex. 3) H CH₃3-Cl-5-CF₃ 2,4-Cl₂ * racemic 31 (Ex. 4) H CH₃ 3-Cl-5-CF₃ 2,4-Cl₂ 110-111(+)-enantiomer 36 (Ex. 6) H CH₃ 3,5-Cl₂ 2,4-Cl₂ * racemic 37 (Ex. 5) HCH₃ 3-Cl-5-Br 2,4-Cl₂ * racemic 38 H CH₃ 3-Cl-5-CF₃ 2,4-Cl₂ *(−)-enantiomer

[0186] INDEX TABLE C

Compound Number (R⁵)_(m) (R⁶)_(p) m.p. (° C.) 32 6-Cl 2-Me 105-106 336-OC₆H₄(3-CF₃) 2-Me 90-91

[0187] INDEX TABLE D

Compound Number (R⁵)_(m) (R⁶)_(p) m.p. (° C.) 34 3-Cl-5-CF₃ 2-Cl-6-OMe *35 3-Cl-5-CF₃ 3,5-Cl₂ *

[0188] INDEX TABLE E Cmpd No. ¹H NMR Data(300mHz; CDCl₃ solution unlessindicated otherwise)^(a) 5 δ 4.95(m, 2H), 7.44(m, 1H), 8.0(s, 1H),8.2-8.3(m, 2H), 8.5(m, 1H), 8.8(m, 1H) 7 (DMSO-d₆) δ 4.8(m, 2H), 8.54(s,1H), 8.55(s, 1H), 8.84(s, 1H), 8.9(s, 1H), 9.5(bs, 1H) 8 δ 2.57(s, 3H),4.96(m, 2H), 7.22(s, 1H), 7.48(bs, 1H), 8.00(s, 1H), 8.71(s, 1H) 18 δ4.95(m, 2H), 7.76(m, 1H), 7.94(bs, 1H), 8.00(s, 1H), 8.16(m, 1H),8.74(s, 1H) 19 (DMSO-d₆) δ 2.30(s, 3H), 4.8(m, 2H), 6.3(m, 1H), 8.2(m,1H), 8.47(s, 1H), 8.93(s, 1H), 10.4 (m, 1H), 12.4(bs, 1H) 20 δ 2.80(s,3H), 4.94(m, 2H), 7.4(bs, 1H), 7.6(m, 1H), 8.0(m, 2H), 8.73(s, 1H) 21 δ2.80(s, 3H), 4.95(m, 2H), 7.4(bs, 1H), 7.6(m, 1H), 8.0(m, 2H), 8.72(s,1H) 22 δ 4.97(m, 2H), 7.44(m, 1H), 7.99(s, 1H), 8.71(m, 1H), 8.80(s,1H), 9.42(bs, 1H) 23 δ 3.50(s, 3H), 4.87,(s, 2H), 4.98(m, 2H), 7.79(m,1H), 7.98(s, 1H), 8.38(m, 1H), 8.74(s, 1H), 8.88(bs, 1H) 24 δ 4.70(m,2H), 7.0(bs, 1H), 7.3-4(m, 3H), 7.7-7.8(m, 3H), 7.9(s, 1H), 8.25(m, 1H),8.4(s, 1H) 25 δ 2.73(s, 3H), 4.91(m, 2H), 7.25(m, 1H), 7.4(bs, 1H),7.8(m, 1H), 8.00(s, 1H), 8.73(s, 1H) 26 δ 4.94(m, 2H), 7.80(m, 1H),7.9(bs, 1H), 8.0(s, 1H), 8.40(m, 1H), 8.77(s, 1H), 9.22(s, 1H) 27(DMSO-d₆) δ 4.8(m, 2H), 7.0(m, 1H), 7.3(m, 1H), 7.3(m, 1H), 7.5(m, 1H),7.8(m, 1H), 8.3 (m, 2H), 8.4(m, 1H), 8.5(s, 1H), 8.9(s, 1H), 9.5(m, 1H)30 δ 1.62(d, 3H, J is 6.7Hz), 5.84(m, 1H), 7.35(d, 1H, J is 5.2Hz),7.40(d, 1H, J is 6.9Hz), 7.99 (d, 1H, J is 1.8Hz), 8.34(d, 1H, J is5.2Hz), 8.70(s, 1H) 34 δ 4.00(s, 3H), 4.88,(m, 2H), 7.09(s, 1H), 7.33(m,1H), 7.80(bs, 1H), 8.00(s, 1H), 8.78(s, 1H) 35 δ 4.98(d, 2H, J is 3.8),7.5(bs, 1H), 8.00(s, 1H), 8.58(s, 2H), 8.71(s, 1H). 36 δ 1.58(d, 3H, Jis 6.6Hz), 5.7-5.8(m, 1H), 7.4(m, 2H), 7.77(m, 1H), 8.35(m, 1H), 8.40(m,1H). 37 δ 1.59(d, 3H, J is 6.6Hz), 5.75(m, 1H), 7.3(bs, 1H), 7.34(d, 1H,J is 5.2Hz), 7.91(d, 1H, J is 1.9Hz), 8.33(d, 1H, J is 5.4Hz), 8.49(d,1H, J is 1.9Hz). 38 δ 1.62(d, 3H, J is 6.7Hz), 5.48(m, 1H), 7.35(d, 1H,J is 5.2Hz), 7.40(d, 1H, J is 6.9), 7.99(d, 1H, J is 1.8Hz), 8.34(d, 1H,J is 5.2), 8.70(s, 1H).

BIOLOGICAL EXAMPLES OF THE INVENTION

[0189] General protocol for preparing test suspensions: Test compoundsare first dissolved in acetone in an amount equal to 3% of the finalvolume and then suspended at the desired concentration (in ppm) inacetone and purified water (50/50 mix) containing 250 ppm of thesurfactant Trem® 014 (polyhydric alcohol esters). The resulting testsuspensions are then used in the following tests. Spraying a 200 ppmtest suspension to the point of run-off on the test plants is theequivalent of a rate of 500 g/ha.

TEST A

[0190] The test suspension was sprayed to the point of run-off on wheatseedlings. The following day the seedlings were inoculated with a sporedust of Erysiphe graminis f. sp tritici, (the causal agent of wheatpowdery mildew) and incubated in a growth chamber at 20° C. for 7 days,after which disease ratings were made.

TEST B

[0191] The test suspension was sprayed to the point of run-off on wheatseedlings. The following day the seedlings were inoculated with a sporesuspension of Puccinia recondita (the casual agent of wheat leaf rust)and incubated in a saturated atmosphere at 20° C. for 24 h, and thenmoved to a growth chamber at 20° C. for 6 days, after which diseaseratings were made.

TEST C

[0192] The test suspension was sprayed to the point of run-off on riceseedlings. The following day the seedlings were inoculated with a sporesuspension of Pyricularia oryzae (the causal agent of rice blast) andincubated in a saturated atmosphere at 27° C. for 24 h, and then movedto a growth chamber at 30° C. for 5 days, after which disease ratingswere made.

TEST D

[0193] The test suspension was sprayed to the point of run-off on tomatoseedlings. The following day the seedlings were inoculated with a sporesuspension of Phytophthora infestanis (the causal agent of potato andtomato late blight) and incubated in a saturated atmosphere at 20° C.for 24 h, and then moved to a growth chamber at 20° C. for 5 days, afterwhich disease ratings were made.

TEST E

[0194] The test suspension was sprayed to the point of run-off on grapeseedlings. The following day the seedlings were inoculated with a sporesuspension of Plasmopara viticola (the causal agent of grape downymildew) and incubated in a saturated atmosphere at 20° C. for 24 h,moved to a growth chamber at 20° C. for 6 days, and then incubated in asaturated atmosphere at 20° C. for 24 h, after which disease ratingswere made.

TEST F

[0195] Tomato (or potato) seedlings are inoculated with a sporesuspension of Phytophthora infestans (the causal agent of potato andtomato late blight) and incubated in a saturated atmosphere at 20° C.for 24 h. The next day, test suspension is sprayed to the point ofrun-off and the treated plants are moved to a growth chamber at 20° C.for 5 days, after which disease ratings are made.

TEST G

[0196] Grape seedlings are inoculated with a spore suspension ofPlasmopara viticola (the causal agent of grape downy mildew) andincubated in a saturated atmosphere at 20° C. for 24 h. The next day,test suspension is sprayed to the point of run-off and the treatedplants are moved to a growth chamber at 20° C. for 6 days, and thenincubated in a saturated atmosphere at 20° C. for 24 h, after whichdisease ratings are made.

[0197] Results for Tests A-E are given in Table A. In the table, arating of 100 indicates 100% disease control and a rating of 0 indicatesno disease control (relative to the controls). A dash (−) indicates notest results. ND indicates disease control not determined due tophytotoxicity. In addition to the Tests shown below, compounds of thisinvention (e.g. compounds 2, 5, 8, 28, 29, 30, 31, 35, 36 and 37) areconsidered to have significant curative utility, especially for grapedowny mildew. TABLE A Cmpd Test Test Test Test Test Test Test No. A B CD E F G 1 0 0 0 90 29 2 0 ND — 100 — 99 3 21 28 0 7  8 4 — — — 99 — 5 —19 — —  98 99 6 0 0 — 19 — 7 0 0 — — — 8 0 8 — 100 100 96 9 0 28 0 7  010 0 9 74 16  0 11 0 9 0 7  8 12 0 19 0 7  24 13 0 9 0 3  23 14 0 19 90100  98 15 0 38 30 7  8 16 0 9 100 34  8 17 13 0 0 25  0 18 0 9 80 32  019 0 9 0 7  8 20 0 28 87 25  8 21 69 68 88 16  8 22 0 0 0 7  0 23 72 9 732  8 24 0 0 7 25  8 25 0 9 13 79  16 26 0 32 0 25  0 27 0 0 0 32  16 28— — 0 100 100 97#  37* 29 — — 0 100 100 100* 30 — — 0 100 100 100* 31 —— 0 100 100  100** 32 0 0 0 32 — 33 91 — — 71 — 34 0 44 — 31 — 35 0 30 —100 100 100* 36 0 38 0 100 100 100  37 0 19 0 100 100 100  38 — — — — 69*   0**

What is claimed is:
 1. A compound selected from Formula I and FormulaII, N-oxides and agriculturally suitable salts thereof,

wherein: A is a substituted pyridinyl ring; B is a substituted pyridinylring; W is C═L or SO.; L is O or S; R¹ and R² are each independently H;or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl, eachoptionally substituted; R³ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl or C₃-C₆ cycloalkyl, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl,C₂-C₆ alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl; R⁴ is C₁-C₆alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl, each optionallysubstituted; X is O or S; and n is 1 or 2; provided that when W is C═Oand R¹, R² and R³ are H; then B is other than4-trifluoromethyl-3-pyridinyl, 2-chloro-4-pyridinyl and2,6-dihalo-4-pyridinyl.
 2. A compound of claim 1 wherein A is apyridinyl ring substituted with from 1 to 4 R⁵; B is a pyridinyl ringsubstituted with from 1 to 4 R⁶; R¹ and R² are each independently H; orC₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl, eachoptionally substituted with one or more substituents selected from thegroup consisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino and C₃-C₆cycloalkylamino; R⁴ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl orC₃-C₆ cycloalkyl, each optionally substituted with one or moresubstituents selected from the group consisting of halogen, CN, NO₂,hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄alkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈dialkylamino and C₃-C₆ cycloalkylamino; R⁵ and R⁶ are each independentlyC₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl,halogen, CN, CO₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy,C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl C₁-C₄haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, C₃-C₆ trialkylsilyl; orR⁵ and R⁶ are each independently phenyl, benzyl or phenoxy, eachoptionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl,C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl,C₃-C₆ halocycloalkyl halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy,C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl C₁-C₄alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl,C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈dialkylaminocarbonyl or C₃-C₆ trialkylsilyl.
 3. A compound of claim 2 ofFormula I wherein W is C═O.
 4. A compound of claim 3 wherein A is asubstituted 3-pyridinyl ring.
 5. A compound of claim 3 wherein A is a2-pyridinyl ring substituted with from 1 to 4 R⁵; and B is substitutedwith from 1 to 4 R⁶, with at least one R⁶ located in a position ortho tothe link with W.
 6. A compound of claim 5 wherein B is either a3-pyridinyl ring or 4-pyridinyl ring having an R⁶ at each position orthoto the link with W and optionally 1 to 2 additional R⁶.
 7. A compound ofclaim 6 wherein each R⁶ is either halogen or methyl.
 8. A compound ofclaim 7 wherein B is a 3-pyridinyl ring wherein one R⁶ is Cl and islocated at the 2-position ortho to the link with W, another R⁶ isselected from Cl or methyl and is located at the 4-position ortho to thelink with W and a third optional R⁶ is methyl at the 6-position.
 9. Thecompound of claim 8 wherein A is 3-chloro-5-CF₃-2-pyridinyl.
 10. Thecompound of claim 5 or claim 7 wherein R¹ is H and R² is CH₃.
 11. Thecompound of claim 2 selected from the group consisting of2,4-Dichloro-N-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl]-3-pyridinecarboxamide,2,4-Dichloro-N-[1-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl]-3-pyridinecarboxamide,2,4-Dichloro-N-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl]-6-methyl-3-pyridinecarboxamide,and2,4-Dichloro-N-[1-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl]-6-methyl-3-pyridinecarboxamide.12. A compound of claim 2 of Formula II wherein A is a 2-pyridinyl ringsubstituted with from 1 to 4 R⁵; and B is substituted with from 1 to 4R⁶, with at least one R⁶ located in a position ortho to the link withthe carbon that is bonded to both X and B.
 13. A compound of claim 12wherein X is S.
 14. A compound of claim 2 of Formula I wherein each R⁵is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy,C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄ alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl,C₃-C₆ trialkylsilyl; provided that when A is 2-pyridinyl, then R⁵ isother than C₁ to C₆ haloalkyl; and each R⁶ is independently C₁-C₆ alkyl,C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalklyl, halogen, CN,CO₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, C₃-C₆ trialkylsilyl; orR⁵ and R⁶ are each independently phenyl, benzyl or phenoxy, eachoptionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl,C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl,C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy,C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl C₁-C₄alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl,C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈dialkylaminocarbonyl or C₃-C₆ trialkylsilyl.
 15. A compound of claim 14wherein W is C═O; each R⁵ is independently C₁-C₆ allyl, C₂-C₆ alkenyl,C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂,hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkoxycarbonyl, C₁-C₄alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈dialkylaminocarbonyl, C₃-C₆ trialkylsilyl; provided that when A is2-pyridinyl, then R⁵ is other than C₁ to C₆ haloalkyl.
 16. A compound ofclaim 15 wherein R⁵ is Cl, Br, CH₃, OCF₃, OCHF₂, OCH₂CF₃, OCF₂CF₃,OCF₂CF₂H, OCHFCF₃, SCF₃, SCHF₂, SCH₂CF₃, SCF₂CF₃, SCF₂CF₂H, SCHFCF₃,SOCF₃, SOCHF₂, SOCH₂CF₃, SOCF₂CF₃, SOCF₂CF₂H, SOCHFCF₃, SO₂CF₃, SO₂CHF₂,SO₂CH₂CF₃, SO₂CF₂CF₃, SO₂CF₂CF₂H or SO₂CHFCF₃.
 17. The compound of claim16 selected from the group consisting of2,4-Dichloro-N-[(3,5-dichloro-2-pyridinyl)methyl]-3-pyridinecarboxamide,2,4-Dichloro-N-[1-(3,5-dichloro-2-pyridinyl)ethyl]-3-pyridinecarboxamide,2,4-Dichloro-N-[(3,5-dichloro-2-pyridinyl)methyl]-6-methyl-3-pyridinecarboxamide,2,4-Dichloro-N-[1-(3,5-dichloro-2-pyridinyl)ethyl]-6-methyl-3-pyridinecarboxamide,N-[(5-bromo-3-chloro-2-pyridinyl)methyl]-2,4-dichloro-3-pyridinecarboxamide,N-[1-(5-bromo-3-chloro-2-pyridinyl)ethyl]-2,4-dichloro-3-pyridinecarboxamide,N-[(5-bromo-3-chloro-2-pyridinyl)methyl]-2,4-dichloro-6-methyl-3-pyridinecarboxamide,andN-[1-(5-bromo-3-chloro-2-pyridinyl)ethyl]-2,4-dichloro-6-methyl-3-pyridinecarboxamide.18. A fungicidal composition comprising a fungicidally effective amountof a compound of claim 1 and at least one additional component selectedfrom the group consisting of surfactants, solid diluents or liquiddiluents.
 19. A fungicidal composition comprising a mixture of acompound of claim 1 and at least one other fungicide having a differentmode of action.
 20. A method for controlling plant diseases caused byfungal plant pathogens comprising applying to the plant or portionthereof, or to the plant seed or seedling, a fungicidally effectiveamount of a compound of claim 1.